US20070135596A1 - Preparation of substituted bridged indenyl and related ligands - Google Patents
Preparation of substituted bridged indenyl and related ligands Download PDFInfo
- Publication number
- US20070135596A1 US20070135596A1 US11/302,846 US30284605A US2007135596A1 US 20070135596 A1 US20070135596 A1 US 20070135596A1 US 30284605 A US30284605 A US 30284605A US 2007135596 A1 US2007135596 A1 US 2007135596A1
- Authority
- US
- United States
- Prior art keywords
- substituted
- bromo
- group
- methylinden
- bis
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 239000003446 ligand Substances 0.000 title claims abstract description 199
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 title claims description 192
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 title claims description 176
- 238000002360 preparation method Methods 0.000 title description 7
- 125000001183 hydrocarbyl group Chemical group 0.000 claims abstract description 135
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 63
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims abstract description 62
- 239000000460 chlorine Substances 0.000 claims abstract description 62
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 59
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 claims abstract description 57
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 45
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 41
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract description 34
- 125000005843 halogen group Chemical group 0.000 claims abstract description 31
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 29
- 125000004104 aryloxy group Chemical group 0.000 claims abstract description 29
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 29
- 125000003367 polycyclic group Chemical group 0.000 claims abstract description 28
- 230000000737 periodic effect Effects 0.000 claims abstract description 27
- 238000005859 coupling reaction Methods 0.000 claims abstract description 26
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims abstract description 25
- 238000004519 manufacturing process Methods 0.000 claims abstract description 25
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 claims abstract description 25
- 230000003647 oxidation Effects 0.000 claims abstract description 20
- 238000007254 oxidation reaction Methods 0.000 claims abstract description 20
- 125000002950 monocyclic group Chemical group 0.000 claims abstract description 18
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 16
- 239000012634 fragment Substances 0.000 claims abstract description 16
- 150000002902 organometallic compounds Chemical class 0.000 claims abstract description 8
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims abstract description 6
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims abstract description 6
- -1 poly(ethylene glycol) Polymers 0.000 claims description 261
- 238000000034 method Methods 0.000 claims description 137
- 230000008569 process Effects 0.000 claims description 105
- ZSWFCLXCOIISFI-UHFFFAOYSA-N endo-cyclopentadiene Natural products C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 claims description 96
- 125000001424 substituent group Chemical group 0.000 claims description 76
- 229910052796 boron Inorganic materials 0.000 claims description 59
- 125000000058 cyclopentadienyl group Chemical group C1(=CC=CC1)* 0.000 claims description 50
- 125000004429 atom Chemical group 0.000 claims description 49
- 239000003054 catalyst Substances 0.000 claims description 49
- 229910052718 tin Inorganic materials 0.000 claims description 43
- 229910052725 zinc Inorganic materials 0.000 claims description 42
- 125000003118 aryl group Chemical group 0.000 claims description 40
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 40
- 125000005842 heteroatom Chemical group 0.000 claims description 34
- 229910052710 silicon Inorganic materials 0.000 claims description 31
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 30
- 229910052793 cadmium Inorganic materials 0.000 claims description 28
- 229910052753 mercury Inorganic materials 0.000 claims description 28
- 229920000642 polymer Polymers 0.000 claims description 27
- 229910052739 hydrogen Inorganic materials 0.000 claims description 26
- 150000001336 alkenes Chemical class 0.000 claims description 25
- 239000001257 hydrogen Substances 0.000 claims description 25
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 20
- 230000008878 coupling Effects 0.000 claims description 19
- 238000010168 coupling process Methods 0.000 claims description 19
- 229920006395 saturated elastomer Polymers 0.000 claims description 18
- 229910052723 transition metal Inorganic materials 0.000 claims description 18
- 150000003624 transition metals Chemical class 0.000 claims description 18
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims description 16
- 229910052757 nitrogen Inorganic materials 0.000 claims description 15
- 229910052708 sodium Inorganic materials 0.000 claims description 15
- 229910052790 beryllium Inorganic materials 0.000 claims description 14
- 229910052792 caesium Inorganic materials 0.000 claims description 14
- 229910052791 calcium Inorganic materials 0.000 claims description 14
- 125000003936 heterocyclopentadienyl group Chemical group 0.000 claims description 14
- 229910052744 lithium Inorganic materials 0.000 claims description 14
- 229910052749 magnesium Inorganic materials 0.000 claims description 14
- 229910052700 potassium Inorganic materials 0.000 claims description 14
- 229910052701 rubidium Inorganic materials 0.000 claims description 14
- 229910052712 strontium Inorganic materials 0.000 claims description 14
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 13
- 125000004122 cyclic group Chemical group 0.000 claims description 12
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 11
- 229910052717 sulfur Inorganic materials 0.000 claims description 11
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 10
- 238000006243 chemical reaction Methods 0.000 claims description 10
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 10
- 229910052760 oxygen Inorganic materials 0.000 claims description 9
- 125000000623 heterocyclic group Chemical group 0.000 claims description 8
- 229910052698 phosphorus Inorganic materials 0.000 claims description 8
- 230000002194 synthesizing effect Effects 0.000 claims description 8
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 7
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 7
- 230000000379 polymerizing effect Effects 0.000 claims description 7
- MUALRAIOVNYAIW-UHFFFAOYSA-N binap Chemical compound C1=CC=CC=C1P(C=1C(=C2C=CC=CC2=CC=1)C=1C2=CC=CC=C2C=CC=1P(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 MUALRAIOVNYAIW-UHFFFAOYSA-N 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- QOPABJOZVXZFJG-UHFFFAOYSA-N 4-diphenylphosphanylphenol Chemical compound C1=CC(O)=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 QOPABJOZVXZFJG-UHFFFAOYSA-N 0.000 claims description 3
- VPLLTGLLUHLIHA-UHFFFAOYSA-N dicyclohexyl(phenyl)phosphane Chemical compound C1CCCCC1P(C=1C=CC=CC=1)C1CCCCC1 VPLLTGLLUHLIHA-UHFFFAOYSA-N 0.000 claims description 3
- 229920001223 polyethylene glycol Polymers 0.000 claims description 3
- 125000001246 bromo group Chemical group Br* 0.000 claims 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 312
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 300
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 189
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 180
- UBHZUDXTHNMNLD-UHFFFAOYSA-N dimethylsilane Chemical compound C[SiH2]C UBHZUDXTHNMNLD-UHFFFAOYSA-N 0.000 description 157
- 239000000203 mixture Substances 0.000 description 150
- 239000001294 propane Substances 0.000 description 150
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 124
- 0 C1=Cc2ccc(CCc3ccc4c3C=CC=C4)c2C=C1.C1=Cc2ccc(CCc3ccc4c3C=CC=C4)c2C=C1.C[Zr](C)(Cl)Cl.C[Zr](C)(Cl)Cl.c1ccc2cccc2c1 Chemical compound C1=Cc2ccc(CCc3ccc4c3C=CC=C4)c2C=C1.C1=Cc2ccc(CCc3ccc4c3C=CC=C4)c2C=C1.C[Zr](C)(Cl)Cl.C[Zr](C)(Cl)Cl.c1ccc2cccc2c1 0.000 description 105
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 102
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 97
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 81
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 72
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 67
- 239000007787 solid Substances 0.000 description 50
- 230000015572 biosynthetic process Effects 0.000 description 48
- 238000005160 1H NMR spectroscopy Methods 0.000 description 46
- 125000003114 inden-1-yl group Chemical group [H]C1=C([H])C([H])(*)C2=C([H])C([H])=C([H])C([H])=C12 0.000 description 41
- YMWUJEATGCHHMB-DICFDUPASA-N dichloromethane-d2 Chemical compound [2H]C([2H])(Cl)Cl YMWUJEATGCHHMB-DICFDUPASA-N 0.000 description 40
- 150000003254 radicals Chemical class 0.000 description 38
- 238000003786 synthesis reaction Methods 0.000 description 35
- 239000000047 product Substances 0.000 description 34
- 125000001624 naphthyl group Chemical group 0.000 description 33
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 30
- 125000004125 inden-2-yl group Chemical group [H]C1=C(*)C([H])([H])C2=C([H])C([H])=C([H])C([H])=C12 0.000 description 29
- 238000010992 reflux Methods 0.000 description 29
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 28
- IJKVHSBPTUYDLN-UHFFFAOYSA-N dihydroxy(oxo)silane Chemical compound O[Si](O)=O IJKVHSBPTUYDLN-UHFFFAOYSA-N 0.000 description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 24
- 239000011701 zinc Substances 0.000 description 24
- 238000004009 13C{1H}-NMR spectroscopy Methods 0.000 description 22
- 239000012300 argon atmosphere Substances 0.000 description 22
- 150000001721 carbon Chemical group 0.000 description 22
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 21
- 239000003153 chemical reaction reagent Substances 0.000 description 20
- 239000003480 eluent Substances 0.000 description 20
- 238000003818 flash chromatography Methods 0.000 description 20
- BWHDROKFUHTORW-UHFFFAOYSA-N tritert-butylphosphane Chemical compound CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 0.000 description 20
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 18
- FQXROCKRFNKCIS-UHFFFAOYSA-N bis(4-bromo-2,5-dimethyl-1h-inden-1-yl)-dimethylsilane Chemical compound CC1=CC(C(=C(C)C=C2)Br)=C2C1[Si](C)(C)C1C(C=CC(C)=C2Br)=C2C=C1C FQXROCKRFNKCIS-UHFFFAOYSA-N 0.000 description 18
- 239000011521 glass Substances 0.000 description 18
- 239000011592 zinc chloride Substances 0.000 description 17
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 17
- DUNKXUFBGCUVQW-UHFFFAOYSA-J zirconium tetrachloride Chemical compound Cl[Zr](Cl)(Cl)Cl DUNKXUFBGCUVQW-UHFFFAOYSA-J 0.000 description 17
- 229910007932 ZrCl4 Inorganic materials 0.000 description 16
- 239000012190 activator Substances 0.000 description 16
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 15
- 229910000027 potassium carbonate Inorganic materials 0.000 description 15
- 239000004711 α-olefin Substances 0.000 description 15
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 14
- 239000000706 filtrate Substances 0.000 description 14
- 238000003756 stirring Methods 0.000 description 14
- VPGLGRNSAYHXPY-UHFFFAOYSA-L zirconium(2+);dichloride Chemical compound Cl[Zr]Cl VPGLGRNSAYHXPY-UHFFFAOYSA-L 0.000 description 14
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 13
- 239000002904 solvent Substances 0.000 description 13
- 239000012044 organic layer Substances 0.000 description 12
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 12
- UQRONKZLYKUEMO-UHFFFAOYSA-N 4-methyl-1-(2,4,6-trimethylphenyl)pent-4-en-2-one Chemical group CC(=C)CC(=O)Cc1c(C)cc(C)cc1C UQRONKZLYKUEMO-UHFFFAOYSA-N 0.000 description 11
- PBAYDYUZOSNJGU-UHFFFAOYSA-N chelidonic acid Natural products OC(=O)C1=CC(=O)C=C(C(O)=O)O1 PBAYDYUZOSNJGU-UHFFFAOYSA-N 0.000 description 11
- 150000001875 compounds Chemical class 0.000 description 11
- 239000011734 sodium Substances 0.000 description 11
- 238000006880 cross-coupling reaction Methods 0.000 description 10
- 238000004508 fractional distillation Methods 0.000 description 9
- 125000000524 functional group Chemical group 0.000 description 9
- 239000000178 monomer Substances 0.000 description 9
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 8
- RZJHSNWOXNTSRU-UHFFFAOYSA-N bis(4-bromo-2-methyl-1h-inden-1-yl)-dimethylsilane Chemical compound CC1=CC(C(=CC=C2)Br)=C2C1[Si](C)(C)C1C(C=CC=C2Br)=C2C=C1C RZJHSNWOXNTSRU-UHFFFAOYSA-N 0.000 description 8
- TUQAMOLMNJWDKY-UHFFFAOYSA-N bis(4-bromo-2-methyl-6-propan-2-yl-1h-inden-1-yl)-dimethylsilane Chemical compound CC1=CC(C(=CC(=C2)C(C)C)Br)=C2C1[Si](C)(C)C1C(C=C(C=C2Br)C(C)C)=C2C=C1C TUQAMOLMNJWDKY-UHFFFAOYSA-N 0.000 description 8
- 239000011575 calcium Substances 0.000 description 8
- 239000011777 magnesium Substances 0.000 description 8
- 229920000098 polyolefin Polymers 0.000 description 8
- 238000006467 substitution reaction Methods 0.000 description 8
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 7
- 239000005977 Ethylene Substances 0.000 description 7
- URTHLAZDNPNYOY-UHFFFAOYSA-N bis(3-bromo-5-methyl-6h-cyclopenta[b]thiophen-6-yl)-dimethylsilane Chemical class BrC1=CSC2=C1C=C(C)C2[Si](C)(C)C1C(SC=C2Br)=C2C=C1C URTHLAZDNPNYOY-UHFFFAOYSA-N 0.000 description 7
- 239000010410 layer Substances 0.000 description 7
- 229910052751 metal Inorganic materials 0.000 description 7
- 239000002184 metal Substances 0.000 description 7
- 125000002524 organometallic group Chemical group 0.000 description 7
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 7
- 150000003623 transition metal compounds Chemical class 0.000 description 7
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 150000001450 anions Chemical class 0.000 description 6
- 239000012298 atmosphere Substances 0.000 description 6
- 239000012043 crude product Substances 0.000 description 6
- LIKFHECYJZWXFJ-UHFFFAOYSA-N dimethyldichlorosilane Chemical compound C[Si](C)(Cl)Cl LIKFHECYJZWXFJ-UHFFFAOYSA-N 0.000 description 6
- 150000002469 indenes Chemical class 0.000 description 6
- ZIYVHBGGAOATLY-UHFFFAOYSA-N methylmalonic acid Chemical class OC(=O)C(C)C(O)=O ZIYVHBGGAOATLY-UHFFFAOYSA-N 0.000 description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 6
- ANRQGKOBLBYXFM-UHFFFAOYSA-M phenylmagnesium bromide Chemical compound Br[Mg]C1=CC=CC=C1 ANRQGKOBLBYXFM-UHFFFAOYSA-M 0.000 description 6
- 239000012279 sodium borohydride Substances 0.000 description 6
- 229910000033 sodium borohydride Inorganic materials 0.000 description 6
- 239000007858 starting material Substances 0.000 description 6
- 241000349731 Afzelia bipindensis Species 0.000 description 5
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 5
- QDUXDAOCNNEYFI-UHFFFAOYSA-N CBC.CBC Chemical compound CBC.CBC QDUXDAOCNNEYFI-UHFFFAOYSA-N 0.000 description 5
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- YNHIGQDRGKUECZ-UHFFFAOYSA-L bis(triphenylphosphine)palladium(ii) dichloride Chemical compound [Cl-].[Cl-].[Pd+2].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 YNHIGQDRGKUECZ-UHFFFAOYSA-L 0.000 description 5
- 230000003197 catalytic effect Effects 0.000 description 5
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 5
- IHLVCKWPAMTVTG-UHFFFAOYSA-N lithium;carbanide Chemical compound [Li+].[CH3-] IHLVCKWPAMTVTG-UHFFFAOYSA-N 0.000 description 5
- GRWIABMEEKERFV-UHFFFAOYSA-N methanol;oxolane Chemical compound OC.C1CCOC1 GRWIABMEEKERFV-UHFFFAOYSA-N 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 150000003613 toluenes Chemical class 0.000 description 5
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 4
- URZXNZKNLBFVAO-UHFFFAOYSA-N 7-bromo-2,6-dimethyl-1h-indene Chemical class C1=C(C)C(Br)=C2CC(C)=CC2=C1 URZXNZKNLBFVAO-UHFFFAOYSA-N 0.000 description 4
- KCWZBTAORNNKFH-UHFFFAOYSA-N 7-chloro-2-methyl-1h-indene Chemical compound C1=CC(Cl)=C2CC(C)=CC2=C1 KCWZBTAORNNKFH-UHFFFAOYSA-N 0.000 description 4
- 239000004215 Carbon black (E152) Substances 0.000 description 4
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- 238000006619 Stille reaction Methods 0.000 description 4
- 238000006069 Suzuki reaction reaction Methods 0.000 description 4
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 4
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 4
- 150000001993 dienes Chemical class 0.000 description 4
- UPQZOUHVTJNGFK-UHFFFAOYSA-N diethyl 2-methylpropanedioate Chemical compound CCOC(=O)C(C)C(=O)OCC UPQZOUHVTJNGFK-UHFFFAOYSA-N 0.000 description 4
- 238000009826 distribution Methods 0.000 description 4
- CRHWEIDCXNDTMO-UHFFFAOYSA-N ditert-butylphosphane Chemical compound CC(C)(C)PC(C)(C)C CRHWEIDCXNDTMO-UHFFFAOYSA-N 0.000 description 4
- 239000000284 extract Substances 0.000 description 4
- 150000004795 grignard reagents Chemical class 0.000 description 4
- 229930195733 hydrocarbon Natural products 0.000 description 4
- BVUQKCCKUOSAEV-UHFFFAOYSA-M magnesium;methylbenzene;bromide Chemical compound [Mg+2].[Br-].CC1=CC=[C-]C=C1 BVUQKCCKUOSAEV-UHFFFAOYSA-M 0.000 description 4
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- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 2
- 239000000920 calcium hydroxide Substances 0.000 description 2
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 2
- 150000001768 cations Chemical class 0.000 description 2
- 239000012230 colorless oil Substances 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- LPIQUOYDBNQMRZ-UHFFFAOYSA-N cyclopentene Chemical compound C1CC=CC1 LPIQUOYDBNQMRZ-UHFFFAOYSA-N 0.000 description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 2
- 230000005595 deprotonation Effects 0.000 description 2
- 238000010537 deprotonation reaction Methods 0.000 description 2
- PPQREHKVAOVYBT-UHFFFAOYSA-H dialuminum;tricarbonate Chemical compound [Al+3].[Al+3].[O-]C([O-])=O.[O-]C([O-])=O.[O-]C([O-])=O PPQREHKVAOVYBT-UHFFFAOYSA-H 0.000 description 2
- HHKIBTQTEOHEJU-UHFFFAOYSA-N dicyclohexyl(phenanthren-9-yl)phosphane Chemical compound C1CCCCC1P(C=1C2=CC=CC=C2C2=CC=CC=C2C=1)C1CCCCC1 HHKIBTQTEOHEJU-UHFFFAOYSA-N 0.000 description 2
- OZIJRVRERJTEGQ-UHFFFAOYSA-N dimethyl-bis(2-methyl-4-phenyl-1h-inden-1-yl)silane Chemical compound CC1=CC(C(=CC=C2)C=3C=CC=CC=3)=C2C1[Si](C)(C)C1C(C)=CC2=C1C=CC=C2C1=CC=CC=C1 OZIJRVRERJTEGQ-UHFFFAOYSA-N 0.000 description 2
- CNXMDTWQWLGCPE-UHFFFAOYSA-N ditert-butyl-(2-phenylphenyl)phosphane Chemical group CC(C)(C)P(C(C)(C)C)C1=CC=CC=C1C1=CC=CC=C1 CNXMDTWQWLGCPE-UHFFFAOYSA-N 0.000 description 2
- LDLDYFCCDKENPD-UHFFFAOYSA-N ethenylcyclohexane Chemical compound C=CC1CCCCC1 LDLDYFCCDKENPD-UHFFFAOYSA-N 0.000 description 2
- BBWMASBANDIFMV-UHFFFAOYSA-N ethyl 4-phenylpiperidine-4-carboxylate;hydrochloride Chemical compound [Cl-].C=1C=CC=CC=1C1(C(=O)OCC)CC[NH2+]CC1 BBWMASBANDIFMV-UHFFFAOYSA-N 0.000 description 2
- KTWOOEGAPBSYNW-UHFFFAOYSA-N ferrocene Chemical compound [Fe+2].C=1C=C[CH-]C=1.C=1C=C[CH-]C=1 KTWOOEGAPBSYNW-UHFFFAOYSA-N 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 125000001590 germanediyl group Chemical group [H][Ge]([H])(*)* 0.000 description 2
- 229910052735 hafnium Inorganic materials 0.000 description 2
- VBJZVLUMGGDVMO-UHFFFAOYSA-N hafnium atom Chemical compound [Hf] VBJZVLUMGGDVMO-UHFFFAOYSA-N 0.000 description 2
- YYLACZAXCCJCJO-UHFFFAOYSA-N heptacos-1-ene Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCC=C YYLACZAXCCJCJO-UHFFFAOYSA-N 0.000 description 2
- 125000001072 heteroaryl group Chemical group 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 2
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 2
- OTUWUWOJDWSEHL-UHFFFAOYSA-M magnesium;1h-naphthalen-1-ide;chloride Chemical compound [Mg+2].[Cl-].[C-]1=CC=CC2=CC=CC=C21 OTUWUWOJDWSEHL-UHFFFAOYSA-M 0.000 description 2
- HTJPDOPKPWUNBX-UHFFFAOYSA-M magnesium;2h-thiophen-2-ide;bromide Chemical compound [Mg+2].[Br-].C=1C=[C-]SC=1 HTJPDOPKPWUNBX-UHFFFAOYSA-M 0.000 description 2
- CCERQOYLJJULMD-UHFFFAOYSA-M magnesium;carbanide;chloride Chemical compound [CH3-].[Mg+2].[Cl-] CCERQOYLJJULMD-UHFFFAOYSA-M 0.000 description 2
- IUYHWZFSGMZEOG-UHFFFAOYSA-M magnesium;propane;chloride Chemical compound [Mg+2].[Cl-].C[CH-]C IUYHWZFSGMZEOG-UHFFFAOYSA-M 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000012968 metallocene catalyst Substances 0.000 description 2
- 229910052752 metalloid Inorganic materials 0.000 description 2
- 150000002738 metalloids Chemical class 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- VAMFXQBUQXONLZ-UHFFFAOYSA-N n-alpha-eicosene Natural products CCCCCCCCCCCCCCCCCCC=C VAMFXQBUQXONLZ-UHFFFAOYSA-N 0.000 description 2
- HUMMCEUVDBVXTQ-UHFFFAOYSA-N naphthalen-1-ylboronic acid Chemical compound C1=CC=C2C(B(O)O)=CC=CC2=C1 HUMMCEUVDBVXTQ-UHFFFAOYSA-N 0.000 description 2
- 229910052759 nickel Inorganic materials 0.000 description 2
- QMMRZOWCJAIUJA-UHFFFAOYSA-L nickel dichloride Chemical compound Cl[Ni]Cl QMMRZOWCJAIUJA-UHFFFAOYSA-L 0.000 description 2
- UBMJSQAFNUWJEG-UHFFFAOYSA-N nonacos-1-ene Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCC=C UBMJSQAFNUWJEG-UHFFFAOYSA-N 0.000 description 2
- NHLUYCJZUXOUBX-UHFFFAOYSA-N nonadec-1-ene Chemical compound CCCCCCCCCCCCCCCCCC=C NHLUYCJZUXOUBX-UHFFFAOYSA-N 0.000 description 2
- 230000000269 nucleophilic effect Effects 0.000 description 2
- CCCMONHAUSKTEQ-UHFFFAOYSA-N octadec-1-ene Chemical compound CCCCCCCCCCCCCCCCC=C CCCMONHAUSKTEQ-UHFFFAOYSA-N 0.000 description 2
- 238000006384 oligomerization reaction Methods 0.000 description 2
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 2
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 2
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 2
- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 description 2
- 125000001147 pentyl group Chemical class C(CCCC)* 0.000 description 2
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 2
- 150000003003 phosphines Chemical class 0.000 description 2
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 229920005629 polypropylene homopolymer Polymers 0.000 description 2
- 229920002223 polystyrene Polymers 0.000 description 2
- NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000003586 protic polar solvent Substances 0.000 description 2
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 2
- 125000000168 pyrrolyl group Chemical group 0.000 description 2
- 239000002516 radical scavenger Substances 0.000 description 2
- FGDZQCVHDSGLHJ-UHFFFAOYSA-M rubidium chloride Chemical compound [Cl-].[Rb+] FGDZQCVHDSGLHJ-UHFFFAOYSA-M 0.000 description 2
- AHLATJUETSFVIM-UHFFFAOYSA-M rubidium fluoride Chemical compound [F-].[Rb+] AHLATJUETSFVIM-UHFFFAOYSA-M 0.000 description 2
- CPRMKOQKXYSDML-UHFFFAOYSA-M rubidium hydroxide Chemical compound [OH-].[Rb+] CPRMKOQKXYSDML-UHFFFAOYSA-M 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 2
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 2
- PUZPDOWCWNUUKD-UHFFFAOYSA-M sodium fluoride Chemical compound [F-].[Na+] PUZPDOWCWNUUKD-UHFFFAOYSA-M 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 2
- SYXYWTXQFUUWLP-UHFFFAOYSA-N sodium;butan-1-olate Chemical compound [Na+].CCCC[O-] SYXYWTXQFUUWLP-UHFFFAOYSA-N 0.000 description 2
- 238000010561 standard procedure Methods 0.000 description 2
- 229910052714 tellurium Inorganic materials 0.000 description 2
- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 2
- ZDLBWMYNYNATIW-UHFFFAOYSA-N tetracos-1-ene Chemical compound CCCCCCCCCCCCCCCCCCCCCCC=C ZDLBWMYNYNATIW-UHFFFAOYSA-N 0.000 description 2
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 2
- ARYHTUPFQTUBBG-UHFFFAOYSA-N thiophen-2-ylboronic acid Chemical compound OB(O)C1=CC=CS1 ARYHTUPFQTUBBG-UHFFFAOYSA-N 0.000 description 2
- 125000003944 tolyl group Chemical group 0.000 description 2
- WMZHDICSCDKPFS-UHFFFAOYSA-N triacont-1-ene Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCCC=C WMZHDICSCDKPFS-UHFFFAOYSA-N 0.000 description 2
- RYTWOFDSURETTI-UHFFFAOYSA-N tributyl(naphthalen-1-yl)stannane Chemical compound C1=CC=C2C([Sn](CCCC)(CCCC)CCCC)=CC=CC2=C1 RYTWOFDSURETTI-UHFFFAOYSA-N 0.000 description 2
- UKTDFYOZPFNQOQ-UHFFFAOYSA-N tributyl(thiophen-2-yl)stannane Chemical compound CCCC[Sn](CCCC)(CCCC)C1=CC=CS1 UKTDFYOZPFNQOQ-UHFFFAOYSA-N 0.000 description 2
- FODRQAHKBOUDMR-UHFFFAOYSA-N tributyl-(2,5-dimethylphenyl)stannane Chemical compound CCCC[Sn](CCCC)(CCCC)C1=CC(C)=CC=C1C FODRQAHKBOUDMR-UHFFFAOYSA-N 0.000 description 2
- QZKHZYGJUDMPRW-UHFFFAOYSA-N tributyl-(3,5-dimethylphenyl)stannane Chemical compound CCCC[Sn](CCCC)(CCCC)C1=CC(C)=CC(C)=C1 QZKHZYGJUDMPRW-UHFFFAOYSA-N 0.000 description 2
- OAYCXBDMSSOCJR-UHFFFAOYSA-N tributyl-[3,5-di(propan-2-yl)phenyl]stannane Chemical compound CCCC[Sn](CCCC)(CCCC)C1=CC(C(C)C)=CC(C(C)C)=C1 OAYCXBDMSSOCJR-UHFFFAOYSA-N 0.000 description 2
- SJDSOBWGZRPKSB-UHFFFAOYSA-N tricos-1-ene Chemical compound CCCCCCCCCCCCCCCCCCCCCC=C SJDSOBWGZRPKSB-UHFFFAOYSA-N 0.000 description 2
- BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 description 2
- YWWDBCBWQNCYNR-UHFFFAOYSA-N trimethylphosphine Chemical compound CP(C)C YWWDBCBWQNCYNR-UHFFFAOYSA-N 0.000 description 2
- HVLLSGMXQDNUAL-UHFFFAOYSA-N triphenyl phosphite Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)OC1=CC=CC=C1 HVLLSGMXQDNUAL-UHFFFAOYSA-N 0.000 description 2
- COIOYMYWGDAQPM-UHFFFAOYSA-N tris(2-methylphenyl)phosphane Chemical compound CC1=CC=CC=C1P(C=1C(=CC=CC=1)C)C1=CC=CC=C1C COIOYMYWGDAQPM-UHFFFAOYSA-N 0.000 description 2
- VNDYJBBGRKZCSX-UHFFFAOYSA-L zinc bromide Chemical compound Br[Zn]Br VNDYJBBGRKZCSX-UHFFFAOYSA-L 0.000 description 2
- NMLXKNNXODLJIN-UHFFFAOYSA-M zinc;carbanide;chloride Chemical compound [CH3-].[Zn+]Cl NMLXKNNXODLJIN-UHFFFAOYSA-M 0.000 description 2
- DMXOXIYARNJFAX-KRWDZBQOSA-N (1R)-1-(2,4-dimethylcyclopenta-1,3-dien-1-yl)-2-methyl-1H-indene Chemical compound CC=1[C@@H](C2=CC=CC=C2C=1)C1=C(C=C(C1)C)C DMXOXIYARNJFAX-KRWDZBQOSA-N 0.000 description 1
- QTTAZHREGZZYHR-IBGZPJMESA-N (1R)-1-(2-tert-butyl-4-methylcyclopenta-1,3-dien-1-yl)-2-methyl-1H-indene Chemical compound CC=1[C@@H](C2=CC=CC=C2C=1)C1=C(C=C(C1)C)C(C)(C)C QTTAZHREGZZYHR-IBGZPJMESA-N 0.000 description 1
- BOMYASHDCDJJKB-HXUWFJFHSA-N (1R)-2-methyl-1-(2-methyl-1H-inden-4-yl)-1H-indene Chemical compound CC=1[C@H](C2=CC=CC=C2C=1)C1=C2C=C(CC2=CC=C1)C BOMYASHDCDJJKB-HXUWFJFHSA-N 0.000 description 1
- UBNOEOXYLALRRG-WVQRXBFSSA-N (1R)-2-methyl-1-(3-methylcyclopenta-1,4-dien-1-yl)-1H-indene Chemical compound CC=1[C@@H](C2=CC=CC=C2C=1)C=1C=CC(C=1)C UBNOEOXYLALRRG-WVQRXBFSSA-N 0.000 description 1
- POYYYMZMPZFCOP-QFIPXVFZSA-N (1R)-2-methyl-1-(4-methyl-2-phenylcyclopenta-1,3-dien-1-yl)-1H-indene Chemical compound CC=1[C@@H](C2=CC=CC=C2C=1)C1=C(C=C(C1)C)C1=CC=CC=C1 POYYYMZMPZFCOP-QFIPXVFZSA-N 0.000 description 1
- HWWKHKOPSUROKF-WOJBJXKFSA-N (1R)-4-ethyl-1-[2-[(1R)-4-ethyl-1H-inden-1-yl]ethyl]-1H-indene Chemical compound CCC1=C2C=C[C@H](C2=CC=C1)CC[C@@H]1C=CC2=C(C=CC=C12)CC HWWKHKOPSUROKF-WOJBJXKFSA-N 0.000 description 1
- KJCXDLFDAVLVAF-ZEQRLZLVSA-N (1R)-4-ethyl-1-[2-[(1R)-4-ethyl-1H-inden-1-yl]propan-2-yl]-1H-indene Chemical compound CCC1=C2C=C[C@@H](C2=CC=C1)C(C)(C)[C@H]1C=CC2=C(C=CC=C12)CC KJCXDLFDAVLVAF-ZEQRLZLVSA-N 0.000 description 1
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- VASOMTXTRMYSKD-UHFFFAOYSA-N (2,3,4,5,6-pentafluorophenyl)boronic acid Chemical compound OB(O)C1=C(F)C(F)=C(F)C(F)=C1F VASOMTXTRMYSKD-UHFFFAOYSA-N 0.000 description 1
- AGKRUNQFGMWKLF-UHFFFAOYSA-N (2,7-dibromo-9h-fluoren-9-yl)-(2,4-dimethyl-1h-inden-1-yl)-dimethylsilane Chemical compound C12=CC(Br)=CC=C2C2=CC=C(Br)C=C2C1[Si](C)(C)C1C(C=CC=C2C)=C2C=C1C AGKRUNQFGMWKLF-UHFFFAOYSA-N 0.000 description 1
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- JZJWNUCHYGAUGF-UHFFFAOYSA-N (2,7-dibromo-9h-fluoren-9-yl)-dimethyl-(3-thiophen-2-ylcyclopenta-1,3-dien-1-yl)silane Chemical compound C12=CC(Br)=CC=C2C2=CC=C(Br)C=C2C1[Si](C)(C)C(CC=1)=CC=1C1=CC=CS1 JZJWNUCHYGAUGF-UHFFFAOYSA-N 0.000 description 1
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- 239000012847 fine chemical Substances 0.000 description 1
- 125000003250 fulvenyl group Chemical class C1(=CC=CC1=C)* 0.000 description 1
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- WHYHZFHCWGGCOP-UHFFFAOYSA-N germyl Chemical compound [GeH3] WHYHZFHCWGGCOP-UHFFFAOYSA-N 0.000 description 1
- 125000003800 germyl group Chemical group [H][Ge]([H])([H])[*] 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- JTOGFHAZQVDOAO-UHFFFAOYSA-N henicos-1-ene Chemical compound CCCCCCCCCCCCCCCCCCCC=C JTOGFHAZQVDOAO-UHFFFAOYSA-N 0.000 description 1
- 125000000755 henicosyl group Chemical class [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- GEAWFZNTIFJMHR-UHFFFAOYSA-N hepta-1,6-diene Chemical compound C=CCCCC=C GEAWFZNTIFJMHR-UHFFFAOYSA-N 0.000 description 1
- 125000002818 heptacosyl group Chemical class [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000003187 heptyl group Chemical class [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- PYGSKMBEVAICCR-UHFFFAOYSA-N hexa-1,5-diene Chemical compound C=CCCC=C PYGSKMBEVAICCR-UHFFFAOYSA-N 0.000 description 1
- 125000006038 hexenyl group Chemical class 0.000 description 1
- 125000004051 hexyl group Chemical class [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000005980 hexynyl group Chemical group 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 125000001145 hydrido group Chemical group *[H] 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 150000003949 imides Chemical class 0.000 description 1
- 150000002466 imines Chemical class 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 229910052745 lead Inorganic materials 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 150000007527 lewis bases Chemical class 0.000 description 1
- 125000002463 lignoceryl group Chemical class [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- XGZVUEUWXADBQD-UHFFFAOYSA-L lithium carbonate Chemical compound [Li+].[Li+].[O-]C([O-])=O XGZVUEUWXADBQD-UHFFFAOYSA-L 0.000 description 1
- 229910052808 lithium carbonate Inorganic materials 0.000 description 1
- JILPJDVXYVTZDQ-UHFFFAOYSA-N lithium methoxide Chemical compound [Li+].[O-]C JILPJDVXYVTZDQ-UHFFFAOYSA-N 0.000 description 1
- AZVCGYPLLBEUNV-UHFFFAOYSA-N lithium;ethanolate Chemical compound [Li+].CC[O-] AZVCGYPLLBEUNV-UHFFFAOYSA-N 0.000 description 1
- OTCKOJUMXQWKQG-UHFFFAOYSA-L magnesium bromide Chemical compound [Mg+2].[Br-].[Br-] OTCKOJUMXQWKQG-UHFFFAOYSA-L 0.000 description 1
- 229910001623 magnesium bromide Inorganic materials 0.000 description 1
- 229910001629 magnesium chloride Inorganic materials 0.000 description 1
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
- ORUIBWPALBXDOA-UHFFFAOYSA-L magnesium fluoride Chemical compound [F-].[F-].[Mg+2] ORUIBWPALBXDOA-UHFFFAOYSA-L 0.000 description 1
- 229910001635 magnesium fluoride Inorganic materials 0.000 description 1
- 239000000347 magnesium hydroxide Substances 0.000 description 1
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 1
- AMQDBUIQKQUCKY-UHFFFAOYSA-M magnesium;1,2,3,4,5-pentafluorobenzene-6-ide;bromide Chemical compound [Mg+2].[Br-].FC1=[C-]C(F)=C(F)C(F)=C1F AMQDBUIQKQUCKY-UHFFFAOYSA-M 0.000 description 1
- JOWQNXIISCPKBK-UHFFFAOYSA-M magnesium;1,3,5-trimethylbenzene-6-ide;bromide Chemical compound [Mg+2].[Br-].CC1=CC(C)=[C-]C(C)=C1 JOWQNXIISCPKBK-UHFFFAOYSA-M 0.000 description 1
- SHAKXLPGFQFNJG-UHFFFAOYSA-M magnesium;1,3-bis(trifluoromethyl)benzene-5-ide;bromide Chemical compound [Mg+2].[Br-].FC(F)(F)C1=C[C-]=CC(C(F)(F)F)=C1 SHAKXLPGFQFNJG-UHFFFAOYSA-M 0.000 description 1
- DCQJQVFIEFMTTQ-UHFFFAOYSA-M magnesium;1,3-dimethylbenzene-2-ide;bromide Chemical compound [Mg+2].[Br-].CC1=CC=CC(C)=[C-]1 DCQJQVFIEFMTTQ-UHFFFAOYSA-M 0.000 description 1
- UDWJEJINASVQGJ-UHFFFAOYSA-M magnesium;1-methanidyl-4-methoxybenzene;chloride Chemical compound [Mg+2].[Cl-].COC1=CC=C([CH2-])C=C1 UDWJEJINASVQGJ-UHFFFAOYSA-M 0.000 description 1
- NMQPDYTXGLHYDX-UHFFFAOYSA-M magnesium;1-methanidyl-4-methylbenzene;chloride Chemical compound [Mg+2].[Cl-].CC1=CC=C([CH2-])C=C1 NMQPDYTXGLHYDX-UHFFFAOYSA-M 0.000 description 1
- SBLQDUJYCAMFLH-UHFFFAOYSA-M magnesium;1-methoxypropane;chloride Chemical compound [Mg+2].[Cl-].COCC[CH2-] SBLQDUJYCAMFLH-UHFFFAOYSA-M 0.000 description 1
- YSMZEMQBSONIMJ-UHFFFAOYSA-M magnesium;2-methanidylpropane;chloride Chemical compound [Mg+2].[Cl-].CC(C)[CH2-] YSMZEMQBSONIMJ-UHFFFAOYSA-M 0.000 description 1
- CQRPUKWAZPZXTO-UHFFFAOYSA-M magnesium;2-methylpropane;chloride Chemical compound [Mg+2].[Cl-].C[C-](C)C CQRPUKWAZPZXTO-UHFFFAOYSA-M 0.000 description 1
- AJECZOAMLZFBIN-UHFFFAOYSA-M magnesium;2h-pyridin-2-ide;bromide Chemical compound [Mg+2].[Br-].C1=CC=N[C-]=C1 AJECZOAMLZFBIN-UHFFFAOYSA-M 0.000 description 1
- QUXHCILOWRXCEO-UHFFFAOYSA-M magnesium;butane;chloride Chemical compound [Mg+2].[Cl-].CCC[CH2-] QUXHCILOWRXCEO-UHFFFAOYSA-M 0.000 description 1
- YNLPNVNWHDKDMN-UHFFFAOYSA-M magnesium;butane;chloride Chemical compound [Mg+2].[Cl-].CC[CH-]C YNLPNVNWHDKDMN-UHFFFAOYSA-M 0.000 description 1
- NXPHGHWWQRMDIA-UHFFFAOYSA-M magnesium;carbanide;bromide Chemical compound [CH3-].[Mg+2].[Br-] NXPHGHWWQRMDIA-UHFFFAOYSA-M 0.000 description 1
- VXWPONVCMVLXBW-UHFFFAOYSA-M magnesium;carbanide;iodide Chemical compound [CH3-].[Mg+2].[I-] VXWPONVCMVLXBW-UHFFFAOYSA-M 0.000 description 1
- FRIJBUGBVQZNTB-UHFFFAOYSA-M magnesium;ethane;bromide Chemical compound [Mg+2].[Br-].[CH2-]C FRIJBUGBVQZNTB-UHFFFAOYSA-M 0.000 description 1
- BXBLTKZWYAHPKM-UHFFFAOYSA-M magnesium;methanidyl(trimethyl)silane;chloride Chemical compound [Mg+2].[Cl-].C[Si](C)(C)[CH2-] BXBLTKZWYAHPKM-UHFFFAOYSA-M 0.000 description 1
- SCEZYJKGDJPHQO-UHFFFAOYSA-M magnesium;methanidylbenzene;chloride Chemical compound [Mg+2].[Cl-].[CH2-]C1=CC=CC=C1 SCEZYJKGDJPHQO-UHFFFAOYSA-M 0.000 description 1
- GLLARPADQLRYIC-UHFFFAOYSA-M magnesium;methanidyloxymethane;chloride Chemical compound [Mg+2].[Cl-].CO[CH2-] GLLARPADQLRYIC-UHFFFAOYSA-M 0.000 description 1
- CRGZYKWWYNQGEC-UHFFFAOYSA-N magnesium;methanolate Chemical compound [Mg+2].[O-]C.[O-]C CRGZYKWWYNQGEC-UHFFFAOYSA-N 0.000 description 1
- NDHDFPWRXRXMCL-UHFFFAOYSA-M magnesium;methoxybenzene;chloride Chemical compound [Mg+2].[Cl-].COC1=CC=[C-]C=C1 NDHDFPWRXRXMCL-UHFFFAOYSA-M 0.000 description 1
- YAMQOOCGNXAQGW-UHFFFAOYSA-M magnesium;methylbenzene;bromide Chemical compound [Mg+2].[Br-].CC1=CC=CC=[C-]1 YAMQOOCGNXAQGW-UHFFFAOYSA-M 0.000 description 1
- 125000002960 margaryl group Chemical class [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical compound [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 description 1
- BWWYHSLPXSWCEC-UHFFFAOYSA-N methanolate;rubidium(1+) Chemical compound [Rb+].[O-]C BWWYHSLPXSWCEC-UHFFFAOYSA-N 0.000 description 1
- VDOUFMGXEMLMJX-UHFFFAOYSA-N methoxymethylboronic acid Chemical compound COCB(O)O VDOUFMGXEMLMJX-UHFFFAOYSA-N 0.000 description 1
- MOVBJUGHBJJKOW-UHFFFAOYSA-N methyl 2-amino-5-methoxybenzoate Chemical compound COC(=O)C1=CC(OC)=CC=C1N MOVBJUGHBJJKOW-UHFFFAOYSA-N 0.000 description 1
- ZKUUVVYMPUDTGJ-UHFFFAOYSA-N methyl 5-hydroxy-4-methoxy-2-nitrobenzoate Chemical compound COC(=O)C1=CC(O)=C(OC)C=C1[N+]([O-])=O ZKUUVVYMPUDTGJ-UHFFFAOYSA-N 0.000 description 1
- 125000006178 methyl benzyl group Chemical group 0.000 description 1
- LAQFLZHBVPULPL-UHFFFAOYSA-N methyl(phenyl)silicon Chemical compound C[Si]C1=CC=CC=C1 LAQFLZHBVPULPL-UHFFFAOYSA-N 0.000 description 1
- KTMKRRPZPWUYKK-UHFFFAOYSA-N methylboronic acid Chemical compound CB(O)O KTMKRRPZPWUYKK-UHFFFAOYSA-N 0.000 description 1
- SAWKFRBJGLMMES-UHFFFAOYSA-N methylphosphine Chemical compound PC SAWKFRBJGLMMES-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 150000004947 monocyclic arenes Chemical class 0.000 description 1
- 125000002819 montanyl group Chemical class [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001802 myricyl group Chemical class [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001421 myristyl group Chemical class [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- NRIJBRZYITYLGP-UHFFFAOYSA-N n,n-dimethyl-4-tributylstannylaniline Chemical compound CCCC[Sn](CCCC)(CCCC)C1=CC=C(N(C)C)C=C1 NRIJBRZYITYLGP-UHFFFAOYSA-N 0.000 description 1
- KWHNJSMJWDZDKD-UHFFFAOYSA-N n,n-dimethyloct-7-en-1-amine Chemical compound CN(C)CCCCCCC=C KWHNJSMJWDZDKD-UHFFFAOYSA-N 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- KPTRDYONBVUWPD-UHFFFAOYSA-N naphthalen-2-ylboronic acid Chemical compound C1=CC=CC2=CC(B(O)O)=CC=C21 KPTRDYONBVUWPD-UHFFFAOYSA-N 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- BMGNSKKZFQMGDH-FDGPNNRMSA-L nickel(2+);(z)-4-oxopent-2-en-2-olate Chemical compound [Ni+2].C\C([O-])=C\C(C)=O.C\C([O-])=C\C(C)=O BMGNSKKZFQMGDH-FDGPNNRMSA-L 0.000 description 1
- UQPSGBZICXWIAG-UHFFFAOYSA-L nickel(2+);dibromide;trihydrate Chemical compound O.O.O.Br[Ni]Br UQPSGBZICXWIAG-UHFFFAOYSA-L 0.000 description 1
- ZBRJXVVKPBZPAN-UHFFFAOYSA-L nickel(2+);triphenylphosphane;dichloride Chemical compound [Cl-].[Cl-].[Ni+2].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 ZBRJXVVKPBZPAN-UHFFFAOYSA-L 0.000 description 1
- BFSQJYRFLQUZKX-UHFFFAOYSA-L nickel(ii) iodide Chemical compound I[Ni]I BFSQJYRFLQUZKX-UHFFFAOYSA-L 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 125000000449 nitro group Chemical class [O-][N+](*)=O 0.000 description 1
- 150000002829 nitrogen Chemical class 0.000 description 1
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- 125000002465 nonacosyl group Chemical class [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001196 nonadecyl group Chemical class [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000005187 nonenyl group Chemical class C(=CCCCCCCC)* 0.000 description 1
- 125000001400 nonyl group Chemical class [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000005071 nonynyl group Chemical group C(#CCCCCCCC)* 0.000 description 1
- SJYNFBVQFBRSIB-UHFFFAOYSA-N norbornadiene Chemical compound C1=CC2C=CC1C2 SJYNFBVQFBRSIB-UHFFFAOYSA-N 0.000 description 1
- JFNLZVQOOSMTJK-KNVOCYPGSA-N norbornene Chemical compound C1[C@@H]2CC[C@H]1C=C2 JFNLZVQOOSMTJK-KNVOCYPGSA-N 0.000 description 1
- 125000003518 norbornenyl group Chemical group C12(C=CC(CC1)C2)* 0.000 description 1
- 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 description 1
- 238000012587 nuclear overhauser effect experiment Methods 0.000 description 1
- 238000005935 nucleophilic addition reaction Methods 0.000 description 1
- QEXZDYLACYKGOM-UHFFFAOYSA-N octacos-1-ene Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCC=C QEXZDYLACYKGOM-UHFFFAOYSA-N 0.000 description 1
- 125000005064 octadecenyl group Chemical class C(=CCCCCCCCCCCCCCCCC)* 0.000 description 1
- 125000004365 octenyl group Chemical class C(=CCCCCCC)* 0.000 description 1
- 125000002347 octyl group Chemical class [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000005069 octynyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C#C* 0.000 description 1
- 229920000620 organic polymer Polymers 0.000 description 1
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 1
- BMMGVYCKOGBVEV-UHFFFAOYSA-N oxo(oxoceriooxy)cerium Chemical compound [Ce]=O.O=[Ce]=O BMMGVYCKOGBVEV-UHFFFAOYSA-N 0.000 description 1
- SIWVEOZUMHYXCS-UHFFFAOYSA-N oxo(oxoyttriooxy)yttrium Chemical compound O=[Y]O[Y]=O SIWVEOZUMHYXCS-UHFFFAOYSA-N 0.000 description 1
- INIOZDBICVTGEO-UHFFFAOYSA-L palladium(ii) bromide Chemical compound Br[Pd]Br INIOZDBICVTGEO-UHFFFAOYSA-L 0.000 description 1
- MXQOYLRVSVOCQT-UHFFFAOYSA-N palladium;tritert-butylphosphane Chemical compound [Pd].CC(C)(C)P(C(C)(C)C)C(C)(C)C.CC(C)(C)P(C(C)(C)C)C(C)(C)C MXQOYLRVSVOCQT-UHFFFAOYSA-N 0.000 description 1
- 125000000913 palmityl group Chemical class [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- BDWBGSCECOPTTH-UHFFFAOYSA-N pentacos-1-ene Chemical compound CCCCCCCCCCCCCCCCCCCCCCCC=C BDWBGSCECOPTTH-UHFFFAOYSA-N 0.000 description 1
- 125000002460 pentacosyl group Chemical class [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- 229940102001 zinc bromide Drugs 0.000 description 1
- AMKXMADQMVPOCK-UHFFFAOYSA-M zinc;1-methanidyl-4-methoxybenzene;chloride Chemical compound [Zn+]Cl.COC1=CC=C([CH2-])C=C1 AMKXMADQMVPOCK-UHFFFAOYSA-M 0.000 description 1
- GEWUULKDXWVRPH-UHFFFAOYSA-M zinc;1-methanidyl-4-methylbenzene;chloride Chemical compound [Zn+]Cl.CC1=CC=C([CH2-])C=C1 GEWUULKDXWVRPH-UHFFFAOYSA-M 0.000 description 1
- HGWIBIDYCWTUQD-UHFFFAOYSA-M zinc;2-methanidyl-2-methylpropane;chloride Chemical compound [Zn+]Cl.CC(C)(C)[CH2-] HGWIBIDYCWTUQD-UHFFFAOYSA-M 0.000 description 1
- ZQJYTTPJYLKTTI-UHFFFAOYSA-M zinc;2h-pyridin-2-ide;bromide Chemical compound Br[Zn+].C1=CC=N[C-]=C1 ZQJYTTPJYLKTTI-UHFFFAOYSA-M 0.000 description 1
- HEOMKTNNZDZMJZ-UHFFFAOYSA-M zinc;benzonitrile;bromide Chemical compound Br[Zn+].N#CC1=CC=[C-]C=C1 HEOMKTNNZDZMJZ-UHFFFAOYSA-M 0.000 description 1
- GOWCWQHQMNLGEB-UHFFFAOYSA-M zinc;fluorobenzene;chloride Chemical compound [Zn+]Cl.FC1=CC=[C-]C=C1 GOWCWQHQMNLGEB-UHFFFAOYSA-M 0.000 description 1
- GBNDTYKAOXLLID-UHFFFAOYSA-N zirconium(4+) ion Chemical compound [Zr+4] GBNDTYKAOXLLID-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F17/00—Metallocenes
Definitions
- the present invention relates to a process for preparing substituted bridged indenyl and related ligands, to the substituted ligands prepared in this way and to their use in preparing metallocenes for olefin polymerization catalysts.
- a high weight average molecular weight when accompanied by a narrow molecular weight distribution, provides a polyolefin with high strength properties.
- Ziegler-Natta catalysts systems a transition metal compound co-catalyzed by an aluminum alkyl—are typically capable of producing polyolefins having a high molecular weight, but with a broad molecular weight distribution.
- transition metal compound has one or more cyclopentadienyl ring ligands (typically two)—such transition metal compound being referred to herein as a “metallocene”—which catalyzes the production of olefin monomers to polyolefins.
- a metalocene which catalyzes the production of olefin monomers to polyolefins.
- titanocenes, zirconocenes and hafnocenes have been utilized as the transition metal component in such “metallocene” containing catalyst system for the production of polyolefins and ethylene-alpha-olefin copolymers.
- Catalysts that produce isotactic polyolefins are disclosed in U.S. Pat. No. 4,794,096. This patent discloses a chiral, stereorigid metallocene catalyst which is activated by an alumoxane cocatalyst and which is reported to polymerize olefins to isotactic polyolefin forms.
- Alumoxane co-catalyzed metallocene structures which have been reported to polymerize alpha-olefins stereoregularly include the ethylene bridged bis-indenyl and bis-tetrahydroindenyl titanium and zirconium (IV) catalysts.
- Bridged zirconocenes containing, as ⁇ ligands, indenyl radicals, which bear the bridge in position 1 and which preferably bear a hydrocarbon radical in position 2 and a hydrocarbon radical in position 4, have been found to be particularly highly active and stereoselective catalyst systems (European Patent Publication No. 0567970 A1; European Patent Publication No 0629632 A2).
- the ligand systems used for these highly active metallocenes are prepared from the corresponding indenes.
- substituted bridged indenyl and related chelating ligands containing halogen and/or sulfonate as leaving groups can be converted in a simple manner into substituted bridged indenyl and related chelating ligands which contain hydrocarbyl, substituted hydrocarbyl, halocarbyl, or substituted halocarbyl substituents bound via sp 2 or sp 3 center and which can be further used for the preparation of active compounds and metallocene complexes.
- the present invention resides in a process for preparing a chelating ligand of the formula (II) from a chelating ligand of the formula (I) via an sp 2 -sp 2 or sp 2 -sp 3 coupling reaction with an organometallic compound of formula (III): wherein B is a bridging group that is bonded to L 1 and L 2 in formula (I) and to L 3 and L 4 in formula (II); L 1 is a substituted monocyclic or polycyclic ligand that comprises at least one chlorine, bromine, iodine, or sulfonate substituent, directly bonded to an sp 2 carbon atom of the ring structure of the ligand; L 2 is a monoanionic ligand; or L 2 may, independently, be defined as L 1 ; L 3 is the same group as L 1 , but said at least one chlorine, bromine, iodine, or sulfonate substituent is replaced with a hydro
- L 1 is a substituted indenyl, a substituted heteroindenyl, a substituted fluorenyl, or a substituted heterofluorenyl ligand.
- L 2 is a substituted or unsubstituted monocyclic or polycyclic ligand, preferably a substituted or unsubstitued cyclopentadienyl ligand, a substituted or unsubstituted heterocyclopentadienyl ligand, a substituted or unsubstituted indenyl ligand, a substituted or unsubstituted heteroindenyl ligand, a substituted or unsubstituted fluorenyl ligand, a substituted or unsubstituted heterofluorenyl ligand.
- L 1 comprises at least one chlorine, bromine, or triflate directly bonded to an sp 2 carbon atom of the ring structure of the ligand, and most preferably L 1 comprises at least one bromine or triflate directly bonded to an sp 2 carbon atom of the ring structure of the ligand.
- Ligands of formula (II) have been further used to obtain the respective metallocenes.
- the latter compounds when combined with activators, readily polymerize various unsaturated monomers.
- the numbering scheme for the Periodic Table Groups is the new notation as set out in C HEMICAL AND E NGINEERING N EWS , 63(5), 27 (1985). Note however that in some of the formulae herein the capital letter “B” is used to indicate a bridge. It is not intended that such bridges be limited to boron, even if boron is one of the possible substituents.
- Me is methyl
- t-Bu and t Bu are tertiary butyl
- iPr and i Pr are isopropyl
- Cy is cyclohexyl
- Ph is phenyl.
- hydrocarbyl radical is defined to be C 1 -C 100 radicals, that may be linear, branched, or cyclic, and when cyclic, aromatic or non-aromatic, and include substituted hydrocarbyl radicals, halocarbyl radicals, and substituted halocarbyl radicals, silylcarbyl radicals, and germylcarbyl radicals as these terms are defined below.
- Substituted hydrocarbyl radicals are radicals in which at least one hydrogen atom has been substituted with at least one functional group such as NR* 2 , OR*, SeR*, TeR*, PR* 2 , AsR* 2 , SbR* 2 , SR*, BR* 2 , SiR* 3 , GeR* 3 , SnR* 3 , PbR* 3 and the like or where at least one non-hydrocarbon atom or group has been inserted within the hydrocarbyl radical, such as —O—, —S—, —Se—, —Te—, —N(R*)—, ⁇ N—, —P(R*)—, ⁇ P—, —As(R*)—, ⁇ As—, —Sb(R*)—, ⁇ Sb—, —B(R*)—, ⁇ B—, —Si(R*) 2 —, —Ge(R*) 2 —,
- Halocarbyl radicals are radicals in which one or more hydrocarbyl hydrogen atoms have been substituted with at least one halogen (e.g. F, Cl, Br, I) or halogen-containing group (e.g. CF 3 ).
- halogen e.g. F, Cl, Br, I
- halogen-containing group e.g. CF 3
- halocarbyl radicals are radicals in which at least one halocarbyl hydrogen or halogen atom has been substituted with at least one functional group such as NR*2, OR*, SeR*, TeR*, PR* 2 , AsR* 2 , SbR* 2 , SR*, BR* 2 , SiR*3, GeR* 3 , SnR*3, PbR* 3 and the like or where at least one non-carbon atom or group has been inserted within the halocarbyl radical such as —O—, —S—, —Se—, —Te—, —N(R*)—, ⁇ N—, —P(R*)—, ⁇ P—, —As(R*)—, ⁇ As—, —Sb(R*)—, ⁇ Sb—, —B(R*)—, ⁇ B—, —Si(R*) 2 —, —Ge(R*)
- Silylcarbyl radicals are groups in which the silyl functionality is bonded directly to the indicated atom or atoms. Examples include SiH 3 , SiH 2 R*, SiHR* 2 , SiR* 3 , SiH 2 (OR*), SiH(OR*) 2 , Si(OR*) 3 , SiH 2 (NR* 2 ), SiH(NR* 2 ) 2 , Si(NR* 2 ) 3 , and the like where R* is independently a hydrocarbyl or halocarbyl radical and two or more R* may join together to form a substituted or unsubstituted saturated, partially unsaturated or aromatic cyclic or polycyclic ring structure.
- Germylcarbyl radicals are groups in which the germyl functionality is bonded directly to the indicated atom or atoms. Examples include GeH 3 , GeH 2 R*, GeHR* 2 , GeR 5 3 , GeH 2 (OR*), GeH(OR*) 2 , Ge(OR*) 3 , GeH 2 (NR* 2 ), GeH(NR* 2 ) 2 , Ge(NR* 2 ) 3 , and the like where R* is independently a hydrocarbyl or halocarbyl radical and two or more R* may join together to form a substituted or unsubstituted saturated, partially unsaturated or aromatic cyclic or polycyclic ring structure.
- Polar radicals, functional groups, or polar groups are groups in which the heteroatom functionality is bonded directly to the indicated atom or atoms. They include heteroatoms of groups 1-17 of the periodic table either alone or connected to other elements by covalent or other interactions such as ionic, van der Waals forces, or hydrogen bonding.
- Examples of functional groups include carboxylic acid, acid halide, carboxylic ester, carboxylic salt, carboxylic anhydride, aldehyde and their chalcogen (Group 14) analogues, alcohol and phenol, ether, peroxide and hydroperoxide, carboxylic amide, hydrazide and imide, amidine and other nitrogen analogues of amides, nitrile, amine and imine, azo, nitro, other nitrogen compounds, sulfur acids, selenium acids, thiols, sulfides, sulfoxides, sulfones, phosphines, phosphates, other phosphorus compounds, silanes, boranes, borates, alanes, aluminates.
- chalcogen Group 14
- Functional groups may also be taken broadly to include organic polymer supports or inorganic support material such as alumina, and silica.
- Preferred examples of polar groups include NR*2, OR*, SeR*, TeR*, PR* 2 , AsR* 2 , SbR* 2 , SR*, BR* 2 , SnR* 3 , PbR* 3 and the like where R* is independently a hydrocarbyl, substituted hydrocarbyl, halocarbyl or substituted halocarbyl radical as defined above and two R* may join together to form a substituted or unsubstituted saturated, partially unsaturated or aromatic cyclic or polycyclic ring structure.
- Sulfonate radical is a group in which hydrocarbyl, substituted hydrocarbyl, halocarbyl, or substituted halocarbyl is bonded to sulfur in —O—S( ⁇ O) 2 group.
- Examples include SO 3 Me (mesylate), SO 3 (4-tosyl) (tosylate), SO 3 CF 3 (triflate), SO 3 (n-C 4 F 9 ) (nonaflate) and the like.
- substituted or unsubstituted monocyclic or polycyclic ligand substituted or unsubstituted cyclopentadienyl ligand”, “substituted or unsubstituted heterocyclopentadienyl ligand”, “substituted or unsubstituted indenyl ligand”, “substituted or unsubstituted heteroindenyl ligand”, “substituted or unsubstituted fluorenyl ligand”, “substituted or unsubstituted heterofluorenyl ligand”, “substituted or unsubstituted pentadienyl ligand”, “substituted or unsubstituted allyl ligand”, and “substituted or unsubstituted boratabenzene ligand”, the substitution to the aforementioned ligand may be hydrocarbyl, substituted hydro
- the hydrocarbyl radical is independently selected from methyl, ethyl, ethenyl and isomers of propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl, eicosyl, heneicosyl, docosyl, tricosyl, tetracosyl, pentacosyl, hexacosyl, heptacosyl, octacosyl, nonacosyl, triacontyl, propenyl, butenyl, pentenyl, hexenyl, heptenyl, octenyl, nonenyl, dec
- examples include phenyl, methylphenyl, dimethylphenyl, ethylphenyl, diethylphenyl, propylphenyl, dipropylphenyl, benzyl, methylbenzyl, naphthyl, anthracenyl, cyclopentyl, cyclopentenyl, cyclohexyl, cyclohexenyl, methylcyclohexyl, cycloheptyl, cycloheptenyl, norbornyl, norbornenyl, adamantyl and the like.
- Alkyl, alkenyl and alkynyl radicals listed include all isomers including where appropriate cyclic isomers, for example, butyl includes n-butyl, 2-methylpropyl, 1-methylpropyl, tert-butyl, and cyclobutyl (and analogous substituted cyclopropyls); pentyl includes n-pentyl, cyclopentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 1-ethylpropyl, and neopentyl (and analogous substituted cyclobutyls and cyclopropyls); butenyl includes E and Z forms of 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 1-methyl-2-propenyl, 2-methyl-1-propenyl
- Cyclic compound having substitutions include all isomer forms, for example, methylphenyl would include ortho-methylphenyl, meta-methylphenyl and para-methylphenyl; dimethylphenyl would include 2,3-dimethylphenyl, 2,4-dimethylphenyl, 2,5-dimethylphenyl, 2,6-diphenylmethyl, 3,4-dimethylphenyl, and 3,5-dimethylphenyl.
- cyclopentadienyl indenyl
- fluorenyl cyclopentanaphthyl
- cyclopentanaphthyl also termed benzindenyl
- indenyl can be considered ascyclopentadienyl fused with a benzene ring.
- fluorenyl can be considered a cyclopentadienyl with two phenyl rings fused onto the cyclopentadienyl ring.
- heterocyclopentadienyls heterophenyls, heteropentalenyls, heterocyclopentapentalenyls, heteroindenyls, heterofluorenyls, heterocyclopentanaphthyls, heterocyclopentaindenyls, heterobenzocyclopentaindenyls, and the like, as illustrated below.
- Each structure is drawn and named as an anion.
- heterocyclopentadienyls include:
- heterocyclopentadienyls include 1,3-diazacyclopentadienyl, 1,3-diphosphacyclopentadienyl, 1,3-diarsacyclopentadienyl, 1,3-distibacyclopentadienyl, 1,3-diboracyclopentadienyl, 1,3-azaphosphacyclopentadienyl, 1,3-azaarsacylcopentadienyl, 1,3-azastibacyclopentadienyl, 1,3-azaboracyclopentadienyl, 1,3-arsaphosphacyclopentadienyl, 1,3-arsastibacyclopentadienyl, 1,3-arsaboracyclopentadienyl, 1,3-boraphosphacyclopentadienyl, 1,3-borastibacylcopentadienyl, 1,3-phosphastib
- heterophenyls include:
- heterophenyls include 1-dihydrocarbylaminoboratabenzene, 4-dihydrocarbylamino-1,4-phosphaboratabenzene, 2-dihydrocarbylamino-1,2-azaboratabenzene, 1-hydrocarbyloxyboratabenzene, 4-hydrocarbyloxy-1,4-phosphaboratabenzene, 2-hydrocarbyloxy-1,2-azaboratabenzene, 1-hydrocarbylboratabenzene, 4-hydrocarbyl-1,4-phosphaboratabenzene, and 2-hydrocarbyl-1,2-azaboratabenzene, where hydrocarbyl is a “hydrocarbyl radical” as previously defined.
- heteropentalenyls include:
- heteropentalenyls include cyclopenta[b]selenophenyl, cyclopenta[c]selenophenyl, cyclopenta[b]tellurophenyl, cyclopenta[c]tellurophenyl, 1-hydrocarbylcyclopenta[b]arsolyl, 2-hydrocarbylcyclopenta[c]arsolyl, 1-hydrocarbylcyclopenta[b]stibolyl, 2-hydrocarbylcyclopenta[c]stibolyl, 1-hydrocarbylcyclopenta[b]pyrrolyl, 2-hydrocarbylcyclopenta[c]pyrrolyl, 1-hydrocarbylcyclopenta[b]phospholyl, and 2-hydrocarbylcyclopenta[c]phospholyl, where hydrocarbyl is a “hydrocarbyl radical” as previously defined.
- heterocylopentapentalenyls include the following, where Z and Q independently represent the heteroatoms O, S, Se, or Te, or heteroatom groups, NR**, PR**, AsR**, or SbR** where R** is hydrogen, or a hydrocarbyl, substituted hydrocarbyl, halocarbyl, substituted halocarbyl, silylcarbyl, or germylcarbyl substituent.
- heteroindenyls include cyclopenta[b]arsinyl, cyclopenta[c]arsinyl, cyclopenta[b]stibinyl, cyclopenta[c]stibinyl, 3-dihydrocarbylamino-1,3-benzothiaborollide, 2dihydrocarbylamino-1,2-benzothiaborollide, 3-hydrocarbyloxy-1,3-benzothiaborollide, 2-hydrocarbyloxy-1,2-benzothiaborollide, 3-hydrocarbyl-1,3-benzothiaborollide, and 2-hydrocarbyl-1,2-benzothiaborollide, where hydrocarbyl is a “hydrocarbyl radical” as previously defined.
- heterofluorenyls include:
- heterocyclopentanaphthyls include:
- heterocyclopentanaphthyls include cyclopenta[g]phosphinolyl, cyclopenta[g]isophosphinolyl, cyclopenta[g]arsinolyl, and cyclopenta[g]isoarsinolyl.
- heterocyclopentaindenyls include:
- heterocyclopentaindenyls include 1-hydrocarboncylcyclopenta[f]phosphindolyl, 2-hydrocarboncylcyclopenta[f]isophosphindolyl, 1-hydrocarbylcyclopenta[f]arsindolyl, 2-hydrocarbylcyclopenta[f]isoarsindolyl, indeno[5,6-b]selenophenyl, indeno[5,6-b]tellurophenyl, indeno[5,6-c]selenophenyl, indeno[5,6-c]tellurophenyl, 2-hydrocarbylcylcyclopenta[f]isoindolyl, and 1-hydrocarbylcyclopenta[f]indolyl, where hydrocarbyl is a “hydrocarbyl radical” as previously defined.
- heterobenzocyclopentaindenyls include:
- heterobenzocyclopentaindenyls include 5-hydrocarbylindeno[1,2-b]indolyl and 5-hydrocarbylindeno[2,1-b]indolyl, where hydrocarbyl is a “hydrocarbyl radical” as previously defined.
- arene ligand is used herein to mean an unsaturated cyclic hydrocarbyl ligand that can consist of one ring, or two or more fused or catenated rings.
- the term “monocyclic ligand” is intended to mean any substituted or unsubstituted C 5 to C 100 monoanionic aromatic five-membered or six-membered single ring structure composed of ring carbon atoms, either alone or in combination with one or more ring heteroatoms.
- the term “monocyclic arene ligand” is used herein to mean a substituted or unsubstituted monoanionic C 5 to C 100 hydrocarbyl ligand that contains an aromatic five-membered single hydrocarbyl ring structure (also referred to as a cyclopentadienyl ring).
- polycyclic ligand is intended to mean any substituted or unsubstituted C 5 to C 103 monoanionic partially unsaturated or aromatic multiple fused ring structure containing at least one aromatic five-membered ring structure, said ligand composed of ring carbon atoms, either alone or in combination with one or more ring heteroatoms.
- polycyclic arenyl ligand is used herein to mean a substituted or unsubstituted monoanionic C 8 to C 103 hydrocarbyl ligand that contains an aromatic five-membered hydrocarbyl ring (also referred to as a cyclopentadienyl ring) that is fused to one or two partially unsaturated, or aromatic hydrocarbyl ring structures which may be fused to additional saturated, partially unsaturated, or aromatic hydrocarbyl rings.
- Monocyclic ligands include substituted or unsubstituted heterocyclopentadienyls and heterophenyls.
- Monocyclic arenyl ligands include substituted or unsubstituted cyclopentadienyls.
- Polycyclic ligands include substituted or unsubstituted, partially unsaturated or aromatic heteroindenyls, heteropentalenyls, heterocyclopentapentalenyls, heterofluorenyls, heterocyclopentanaphthyls, heterocyclopentaindenyls, and heterobenzocyclopentaindenyls.
- Polycyclic arenyl ligands include substituted or unsubstituted, partially unsaturated or aromatic indenyls, fluorenyls, and cyclopentanaphthyls.
- Non-limiting examples of polycyclic arene ligands include indenyl, 4,5-dihydroindenyl, 4,7-dihydroindenyl, 4,5,6,7-tetrahydroindenyl, fluorenyl, 1,2-dihydrotetrahydrofluorenyl, 1,4-dihydrotetrahydrofluorenyl, 3,4-dihydrotetrahydrofluorenyl, 1,2,3,4-tetrahydrofluorenyl, 1,2,5,6-tetrahydrofluorenyl, 1,2,7,8-tetrahydrofluorenyl, 3,4,5,6-tetrahydrofluorenyl, 1,4,5,8-tetrahydrofluorenyl, 1,2,3,4,5,6,7,8-octahydrofluorenyl, cyclopenta[b]naphthyl, 4,4a-
- Partially hydrogenated polycyclic arene ligands retain the numbering scheme of the parent polycyclic arene ligand, namely the numbering schemes defined for indenyl, fluorenyl, cyclopenta[b]naphthyl, and cyclopenta[a]naphthyl ligands.
- a “ring heteroatom” is a heteroatom that is within a cyclic ring structure.
- a “heteroatom substituent” is a heteroatom containing group that is directly bonded to a ring structure through the heteroatom.
- the terms “ring heteroatom” and “heteroatom substituent” are illustrated below where Z is a heteroatom group preferably S, O, Se, Te, N—R′, P—R′, As—R′, Sb—R′ or B—R′ and each R 1 is independently a hydrocarbyl, substituted hydrocarbyl, halocarbyl or substituted halocarbyl radical as defined above and two R 1 may join together to form a substituted or unsubstituted saturated, partially unsaturated or aromatic cyclic or polycyclic ring structure.
- R 1 can additionally be a Group 15 or Group 16 group where the heteroatom is directly bonded to boron and R 1 is then preferably an O—R′′ group or an N—R 12 group, where each R′′ is independently a hydrocarbyl, substituted hydrocarbyl, halocarbyl or substituted halocarbyl radical as defined above and two R′′ may join together to form a substituted or unsubstituted saturated, partially unsaturated or aromatic cyclic or polycyclic ring structure.
- a “ring carbon atom” is a carbon atom that is part of a cyclic ring structure. By this definition, an indenyl fragment has nine ring carbon atoms.
- a “bondable ring position” is a ring position that is capable of bearing a substituent or bridging substituent.
- cyclopenta[b]thienyl has five bondable ring positions (at the carbon atoms) and one non-bondable ring position (the sulfur atom);
- cyclopenta[b]pyrrolyl has six bondable ring positions (at the carbon atoms and at the nitrogen atom).
- homopolymerization would produce a polymer made from one monomer.
- homopolymerization of propylene would produce homopolypropylene.
- homopolymerization of ethylene would produce homopolyethylene.
- copolymerization would produce polymers with more than one monomer type.
- ethylene copolymers include polymers of ethylene with ⁇ -olefins, cyclic olefins and diolefins, vinylaromatic olefins, ⁇ -olefinic diolefins, substituted ⁇ -olefins, and/or acetylenically unsaturated monomers.
- Non-limiting examples of ⁇ -olefins include ethylene, propylene, 1-butene, 1-pentene, 1-hexene, 1-heptene, 1-octene, 1-nonene, 1-decene, 1-undecene 1-dodecene, 1-tridecene, 1-tetradecene, 1-pentadecene, 1-hexadecene, 1-heptadecene, 1-octadecene, 1-nonadecene, 1-eicosene, 1-heneicosene, 1-docosene, 1-tricosene, 1-tetracosene, 1-pentacosene, 1-hexacosene, 1-heptacosene, 1-octacosene, 1-nonacosene, 1-triacontene, 4-methyl-1-pentene, 3-methyl-1-pentene, 5-methyl-1-nonene, 3,5,
- Non-limiting examples of cyclic olefins and diolefins include cyclobutene, cyclopentene, cyclohexene, cycloheptene, cyclooctene, cyclononene, cyclodecene, norbornene, 4-methylnorbornene, 2-methylcyclopentene, 4-methylcyclopentene, vinylcyclohexane, norbornadiene, dicyclopentadiene, 5-ethylidene-2-norbornene, vinylcyclohexene, 5-vinyl-2-norbornene, 1,3-divinylcyclopentane, 1,2-divinylcyclohexane, 1,3-divinylcyclohexane, 1,4-divinylcyclohexane, 1,5-divinylcyclooctane, 1-allyl-4-vinylcyclohexane, 1,4-diallylcyclohexane,
- Non-limiting examples of vinylaromatic olefins include styrene, para-methylstyrene, para-t-butylstyrene, vinylnaphthylene, vinyltoluene, and divinylbenzene.
- Non-limiting examples of ⁇ -olefinic dienes include 1,4-hexadiene, 1,5-hexadiene, 1,5-heptadiene, 1,6-heptadiene, 6-methyl-1,6-heptadiene, 1,7-octadiene, 7-methyl-1,7-octadiene, 1,9-decadiene, 1,11-dodecene, 1,13-tetradecene and 9-methyl-1,9-decadiene.
- Substituted ⁇ -olefins include those containing at least one non-carbon Group 13 to 17 atom bound to a carbon atom of the substituted ⁇ -olefin where such substitution if silicon may be adjacent to the double bond or terminal to the double bond, or anywhere in between, and where inclusion of non-carbon and non-silicon atoms such as for example B, O, S, Se, Te, N, P, Ge, Sn, Pb, As, F, Cl, Br, or I, are contemplated, where such non-carbon or non-silicon moieties are sufficiently far removed from the double bond so as not to interfere with the coordination polymerization reaction with the catalyst and so to retain the generally hydrocarbyl characteristic.
- the number of carbon atoms, or the number of carbon and silicon atoms, separating the double bond and the non-carbon or non-silicon moiety is preferably 6 or greater, e.g. 7, or 8, or 9, or 10, or 11, or 12, or 13, or 14 or more.
- the number of such carbon atoms, or carbon and silicon atoms is counted from immediately adjacent to the double bond to immediately adjacent to the non-carbon or non-silicon moiety. Examples include 8,8,8-trifluoro-1-octene, 8-methoxyoct-1-ene, 8-methylsulfanyloct-1-ene, 8-dimethylaminooct-1-ene, or combinations thereof.
- Such monomers permit the preparation of both functional-group containing copolymers capable of subsequent derivatization, and of functional macromers which may be used as graft and block type polymeric segments.
- Copolymerization can also incorporate ⁇ -olefinic macromonomers of up to 2000 mer units.
- oligomer refers to compositions having 2-75 mer units and the term polymer refers to compositions having 76 or more mer units.
- a mer is defined as a unit of an oligomer or polymer that originally corresponded to the monomer(s) used in the oligomerization or polymerization reaction.
- the mer of polyethylene would be ethylene.
- catalyst system is defined to mean a catalyst precursor/activator pair.
- catalyst system means the unactivated catalyst (precatalyst) together with an activator and, optionally, a co-activator.
- activator When it is used to describe such a pair after activation, it means the activated catalyst and the activator or other charge-balancing moiety.
- the transition metal compound may be neutral as in a precatalyst, or a charged species with a counter ion as in an activated catalyst system.
- Catalyst precursor is also often referred to as precatalyst, catalyst, catalyst compound, catalyst precursor, transition metal compound or transition metal complex. These words are used interchangeably.
- Activator and cocatalyst are also used interchangeably.
- a scavenger is a compound that is typically added to facilitate oligomerization or polymerization by scavenging impurities. Some scavengers may also act as activators and may be referred to as co-activators.
- a co-activator, that is not a scavenger, may also be used in conjunction with an activator in order to form an active catalyst. In some embodiments a co-activator can be pre-mixed with the transition metal compound to form an alkylated transition metal compound, also referred to as an alkylated invention compound.
- Noncoordinating anion is defined to mean an anion either that does not coordinate to the catalyst metal cation or that does coordinate to the metal cation, but only weakly.
- An NCA coordinates weakly enough that a neutral Lewis base, such as an olefinically or acetylenically unsaturated monomer can displace it from the catalyst center.
- Any metal or metalloid that can form a compatible, weakly coordinating complex may be used or contained in the noncoordinating anion.
- Suitable metals include, but are not limited to, aluminum, gold, and platinum.
- Suitable metalloids include, but are not limited to, boron, aluminum, phosphorus, and silicon.
- a stoichiometric activator can be either neutral or ionic.
- the terms ionic activator, and stoichiometric ionic activator can be used interchangeably.
- neutral stoichiometric activator, and Lewis acid activator can be used interchangeably.
- the chelating ligands according to the invention can be used to synthesize the respective transition metal derivatives of importance as catalyst components for the production of polymers or oligomers, including homopolymers, such as homopolyethylene or homopolypropylene, copolymers of ethylene with other olefins including alpha-olefins, and copolymers of propylene with other olefins including alpha-olefins.
- the invention provides a process for preparing a chelating ligand of the formula (II) from a chelating ligand of the formula (I) via an sp 2 -sp 2 or sp 2 -sp 3 coupling reaction with an organometallic compound of formula (III): wherein B is a bridging group that is bonded to L 1 and L 2 in formula (I) and to L 3 and L 4 in formula (II); L 1 is a substituted monocyclic or polycyclic ligand that comprises at least one chlorine, bromine, iodine, or sulfonate substituent, directly bonded to an sp 2 carbon atom of the ring structure of the ligand; L 2 is a monoanionic ligand; or L 2 may, independently, be defined as L 1 ; L 3 is the same group as L 1 , but said at least one chlorine, bromine, iodine, or sulfonate substituent is replaced with a hydrocar
- L 1 is a substituted indenyl, a substituted heteroindenyl, a substituted fluorenyl, or a substituted heterofluorenyl ligand.
- L 2 is a substituted or unsubstituted monocyclic or polycyclic ligand, preferably a substituted or unsubstitued cyclopentadienyl ligand, a substituted or unsubstituted heterocyclopentadienyl ligand, a substituted or unsubstituted indenyl ligand, a substituted or unsubstituted heteroindenyl ligand, a substituted or unsubstituted fluorenyl ligand, a substituted or unsubstituted heterofluorenyl ligand.
- L 1 comprises at least one chlorine, bromine, or triflate directly bonded to an sp 2 carbon atom of the ring structure of the ligand, and most preferably L 1 comprises at least one bromine or triflate directly bonded to an sp 2 carbon atom of the ring structure of the ligand.
- the invention provides a process for preparing a chelating ligand of the formula (IIa), (IIb), or (IIc) from a chelating ligand of the formula (Ia), (Ib), or (Ic), respectively: and a coupling component of the formula (III) wherein M 1 is an element of group 1, 2, 12, 13 or 14 of the Periodic Table of the Elements, preferably Li, Na, K, Rb, Cs, Be, Mg, Ca, Sr, Ba, B, Si, Sn, Zn, Cd or Hg, more preferably B, Si, Sn, Zn, Cd or Hg, and most preferably B, Sn or Zn; the or each X 1 is a chlorine, bromine, iodine, triflate, or sulfonate group, preferably chlorine, bromine, or triflate, and more preferably bromine or triflate, and the or each X 1 is directly bonded to an sp 2 carbon atom
- the invention provides a process for preparing a chelating ligand of the formula (Va), (Vb), (Vc), (Vd), (Ve), (Vf), (Vg), (Vh), (Vi), (Vk), (Vm), (Vn), (Vo), (Vp), (Vq), (Vr), (Vs), (Vt), (Vu), (Vv), (Vw), (Vx), or (Vy) from a chelating ligand of the formula (IVa), (IVb), (IVc), (IVd), (IVe), (IVf), (IVg), (IVh), (IVi), (IVk), (UVm), (IVn), (IVo), (IVp), (IVq), (IVr), (IVs), (IVt), (IVu), (IVv), (IVw), (IVx), or (IVy), respectively, and a coupling component of the formula (III): wherein: M 1 is an element of group 1, 2, 12, 13 or 14
- the invention provides a process for preparing a chelating ligand of the formula (VIIa), (VIb), (VIc), (VIId), (VIIe), (VIIf), (VIIg), (VIIh), (VIIi), (VIIk), (VIIm), (VIIn), (VIIo), (VIIp), (VIIq), (VIIr), or (VIs) from a chelating ligand of the formula (VIa), (VIb), (VIc), (VId), (VIe), (VIf), (VIg), (VIh), (VIi), (VIk), (VIm), (VIn), (VIo), (VIp), (VIq), (VIr), or (VIs), respectively, and a coupling component of the formula (III): wherein: M 1 is an element of group 1, 2, 12, 13 or 14 of the Periodic Table of the Elements, preferably Li, Na, K, Rb, Cs, Be, Mg, Ca, Sr, Ba,
- the invention provides a process for preparing a chelating ligand of the formula (IId), (IId), or (IIf) from a chelating ligand of the formula (Id), (Ie), or (If), respectively, and a coupling component of the formula (III): wherein: M 1 is an element of group 1, 2, 12, 13 or 14 of the Periodic Table of the Elements, preferably Li, Na, K, Rb, Cs, Be, Mg, Ca, Sr, Ba, B, Si, Sn, Zn, Cd or Hg, more preferably B, Si, Sn, Zn, Cd or Hg, and most preferably B, Sn or Zn; each X 1 is independently a chlorine, bromine, iodine, triflate, or sulfonate group, preferably chlorine, bromine, or triflate, and more preferably, bromine or triflate, and each X 1 is directly bonded to an sp 2 carbon atom of the
- the invention provides a process for preparing a chelating ligand of the formula (IXa), (IXb), (IXc), (IXd), (IXe), (IXf), (IXg), (IXh), (IXi), or (IXk) from a chelating ligand of the formula (VIIIa), (VIIIb), (VIIIc), (VIIId), (VIIIe), (VIIIf), (VIIIg), (VIIIh), (VIIIi), or (VIIIk), respectively, and a coupling component of the formula (III): wherein: M 1 is an element of group 1, 2, 12, 13 or 14 of the Periodic Table of the Elements, preferably Li, Na, K, Rb, Cs, Be, Mg, Ca, Sr, Ba, B, Si, Sn, Zn, Cd or Hg, more preferably B, Si, Sn, Zn, Cd or Hg, and most preferably B, Sn or Zn;
- B in each of formulae given in all the embodiments of this invention is a bridging group containing boron or a Group 14, 15 or 16 element.
- suitable bridging groups include R′ 2 C, R′ 2 Si, R′ 2 Ge, R′ 2 CCR′ 2 , R′ 2 CCR′ 2 CR′ 2 , R′ 2 CCR′ 2 CR′ 2 CR′ 2 , R′C ⁇ CR′, R′C ⁇ CR′CR′ 2 , R′ 2 CCR′ ⁇ CR′CR′ 2 , R′C ⁇ CR′CR′ ⁇ CR′, R′C ⁇ CR′CR′ 2 CR′ 2 , R′ 2 CSiR′ 2 , R′ 2 SiSiR′ 2 , R′ 2 CSiR′ 2 CR′ 2 , R′ 2 SiCR′ 2 SiR′ 2 , R′C ⁇ CR′SiR′ 2 , R′ 2 CGeR′ 2 , R′ 2 GeGeR′ 2 , R′ 2 CGeR
- Preferred examples for the bridging group Y include CH 2 , CH 2 CH 2 , CH(CH 3 ) 2 , SiMe 2 , SiPh 2 , SiMePh, Si(CH 2 ) 3 , and Si(CH 2 ) 4 .
- Non-limiting examples of chelating ligands of the formula (I) include:
- Aliphatic, heteroaliphatic, aromatic, heteroaromatic, alkenyl, and heteroalkenyl organometallic compounds of the formula (III) are likewise obtainable in a simple manner by standard methods of the prior art or can be purchased commercially.
- the synthesis of organozinc reagents, of importance in Negishi reactions, is described, for example, in Organozinc Reagents , Ed. by P. Knochel, P. Jones, Oxford U Press, 1999.
- the synthesis of boronic acids, of importance in Suzuki-Miyaura reactions is described, for example, in Organic Synthesis, Collective Volume IV , Wiley, 1963.
- the synthesis of organotin reagents, of importance in Stille reactions is described, for example, in V.
- organometallic reagents of the formula (III) involves standard methods of organometallic chemistry and is described, for example, in Organometallics in Synthesis , Ed. By M. Schlosser, and in J. March, Advanced Organic Chemistry, 4 th Edition, 1992 and the references cited therein.
- chelating ligands of the formula (II) which are substituted by hydrocarbyl groups in the six-membered ring of indenes and heteroindenes or in the five-membered heterocyclic ring of cyclopentathiophenes and related fragments is carried out by means of a transition metal-catalyzed sp 2 -sp 3 and sp 2 -sp 2 coupling reaction of halo-substituted chelating ligands of the formula (I) with organometallic reagents of the formula (III).
- reaction are carried out in suitable solvents, such as diethyl ether, tetrahydrofuran, toluene, etc., under an inert gas atmosphere.
- suitable solvents such as diethyl ether, tetrahydrofuran, toluene, etc.
- transition metal complexes of Groups 8 to 10 of the Periodic Table of the Elements preferably Group 10.
- Particularly useful complexes are complexes of nickel and palladium.
- Non-limiting examples of transition metal catalysts include: palladium chloride, palladium bromide, palladium iodide, palladium dibenzylidenacetone, palladium acetate, dichlorobis(triphenylphosphine)palladium, bis(tri-tert-butylphosphine)palladium, dichlorobis(triphenylphosphine)palladium(II), polymer-bound catalysts such as dichlorobis(triphenylphosphine)palladium(II) polymer bound or tetrakis(triphenylphosphine)palladium(0) polymer bound (both are available from Aldrich Chemical Company where the polymer is a divinylbenzene crosslinked polystyrene), nickel chloride, nickel bromide, nickel iodide, nickel acetylacetonate, dichlorobis(triphenylphosphine)nickel, bis(1,5-cyclooctadieny
- the catalyst can be a mixture of one or more of the above mentioned salts and a suitable ligand.
- ligands which may be polymer-supported
- the most preferred ligands for nickel catalyst are: triphenylphosphine, triethylphosphite; 2,2′-bipyridyl and o-phenanthroline.
- the most preferred ligands for palladium catalyst are: tri(tert-butyl)phosphine, (2-biphenyl)di(tert-butyl)phosphine, (2′-dimethylaminobiphenyl-2)di(tert-butyl)phosphine, (9-phenanthrenyl)dicyclohexylphosphine, 1.1′-bis(di-tert-butylphosphino)ferrocene, XANTPHOS, and the carbene ligand shown above.
- Grignard reagents of the formula (III) which are preferred in the process of the present invention include: methylmagnesium chloride, methylmagnesium bromide, methylmagnesium iodide, dimethylmagnesium, ethylmagnesium bromide, n-propylmagnesium chloride, isopropylmagnesium chloride, n-butylmagnesium chloride, sec-butylmagnesium chloride, isobutylmagnesium chloride, tert-butylmagnesium chloride, cyclopentylmagnesium chloride, cyclohexylmagnesium chloride, benzylmagnesium chloride, 4-methylbenzylmagnesium chloride, 4-methoxybenzylmagnesium chloride, 4-trifluoromethyhnagnesium chloride, diphenylmethylmagnesium bromide, adamantylmagnesum bromide, cyclohexenylmagnes
- Grignard reagents are: cyclopentylmagnesium chloride, cyclohexylmagnesium chloride, 2-thienylmagnesium bromide, 3,5-dimethylphenylmagnesium chloride, 2,5-dimethylphenylmagnesium chloride, 3,5-diisopropylphenylmagnesium chloride, 3,5-tert-butylphenylmagnesium chloride, 1-naphthylmagnesium chloride.
- Non-limiting examples of organozinc reagents of the formula (III) which are preferred in the process of the present invention include: methylzinc chloride, methylzinc bromide, methylzinc iodide, dimethylzinc, ethylzinc bromide, n-propylzinc chloride, isopropylzinc chloride, n-butylzinc chloride, sec-butylzinc chloride, isobutylzinc chloride, tert-butylzinc chloride, cyclopentylzinc chloride, cyclohexylzinc chloride, benzylzinc chloride, 4-methylbenzylzinc chloride, 4-methoxybenzylzinc chloride, 4-trifluoromethylzinc chloride, diphenylmethylzinc bromide, adamantylmagnesum bromide, cyclohexenylzinc chloride, isopropenylzinc chloride, 2-phenylethen
- organozinc reagents are: cyclopentylzinc chloride, cyclohexylzinc chloride, 2-thienylzinc bromide, 3,5-dimethylphenylzinc chloride, 2,5-dimethylphenylzinc chloride, 3,5-diisopropylphenylzinc chloride, 3,5-tert-butylphenylzinc chloride, 1-naphthylzinc chloride.
- Non-limiting examples of organoboron reagents of the formula (III) which are preferred in the process of the present invention are: methylboronic acid, ethylboronic acid, n-propylboronic acid, isopropylboronic acid, n-butylboronic acid, sec-butylboronic acid, isobutylboronic acid, tert-butylboronic acid, cyclopentylboronic acid, cyclohexylboronic acid, benzylboronic acid, 4-methylbenzylboronic acid, 4-methoxybenzylboronic acid, 4-trifluoromethylboronic acid, diphenylmethylboronic acid, adamantylboronic acid, cyclohexenylboronic acid, isopropenylboronic acid, 2-phenylethenylboronic acid, trimethylsilylmethylboronic acid, neopentylboronic acid, methoxymethylboronic acid, 3-methoxypropylboronic acid
- organoboron reagents are: 2-thienylboronic acid, 3,5-dimethylphenylboronic acid, 2,5-dimethylphenylboronic acid, 3,5-diisopropylphenylboronic acid, 3,5-tert-butylphenylboronic acid, 1-naphthylboronic acid.
- bases to be used include: potassium carbonate, sodium carbonate, lithium carbonate, cesium carbonate, rubidium carbonate, lithium hydroxide, sodium hydroxide, potassium hydroxide, sodium triphosphate, potassium triphosphate, sodium hydrocarbonate, calcium carbonate, calcium oxide, barium carbonate, barium oxide, aluminium carbonate, aluminium oxide, yttrium carbonate, yttrium oxide, cerium carbonate, cerium oxide, barium hydroxide, calcium hydroxide, yttrium hydroxide, cerium hydroxide, aluminium hydroxide, sodium methylate, sodium ethylate, sodium isopropylate, sodium n-butoxide, sodium tert-butoxide, lithium ethylate, potassium ethylate.
- organotin reagents of the formula (III) which are preferred in the process of the present invention include: tetramethyltin, teraethyltin, tetracyclohexyltin, 2-pyridyl-tri-n-butyltin, 4-pyridyl-tri-n-butyltin, 2-thienyl-tri-n-butyltin, 2-benzothienyl-tri-n-butyltin, 2-benzofuryl-tri-n-butyltin, 3-(N-methylindolyl)-tri-n-butyltin, phenyl-tri-n-butyltin, phenyltrimethyltin, phenyltriethyltin, phenyltriisopropyltin, phenyltriisobutyltin, phenyltricyclohexyltin, tetraphenyltin, 2-
- organotin reagents are: 2-thienyl-tri-n-butyltin, 3,5-dimethylphenyl-tri-n-butyltin, 2,5-dimethylphenyl-tri-n-butyltin, 3,5-diisopropylphenyl-tri-n-butyltin, 3,5-tert-butylphenyl-tri-n-butyltin, 1-naphthyl-tri-n-butyltin.
- the cross-coupling reactions using organotin reagents require the use of a nucleophilic aid agent.
- aiding agents to be used include: lithium fluoride, sodium fluoride, potassium fluoride, rubidium fluoride, cesium fluoride, tetramethylammonium fluoride, tetraethylammonium fluoride, tetra-n-butylammonium fluoride, magnesium fluoride, calcium fluoride, barium fluoride, aluminium fluoride, tetramethylphosphonium fluoride, lithium chloride, sodium bromide, potassium chloride, rubidium chloride, cesium chloride, tetramethylammonium chloride, tetraethylammonium chloride, tetra-n-butylammonium chloride, magnesium chloride, calcium chloride, barium chloride, aluminium chloride, tetramethylphosphonium chloride, lithium hydroxide, sodium
- Non-limiting examples of organometallic compounds of the formula (III), other than Grignard, organozinc, organoboron, and organotin reagents include: dimethylcadmium, diphenylcadmium, trimethylindium, tripenylindium, phenylindium dichloride, trimethylgallium, triphenylgallium, phenylgallium dichloride, tetraphenylsilane, phenyltrichlorosilane, phenyltrimethoxysilane, tetraphenylgermane, phenyltrichlorogermane, phenyltrimethoxygermane, triphenylbismuth, phenylbismuth dichloride, phenylbismuth diethoxide.
- NiCl 2 (dppp) 2 or NiCl 2 (PPh 3 ) 2 in an amount of 0.01 to 5 mol %, preferably 1 to 3 mol % and most preferably about 2 mol %, in each case relative to the chelating ligand of the formula (I) used.
- the particularly preferred catalyst Pd(OAc) 2 in combination with a phosphine or phosphine ligand such as ligands A through N, or Pd(P t Bu 3 ) 2 in an amount of 0.000001 to 5 mol %, preferably 0.01 to 2 mol % and most preferably about 1 mol %, in each case based on the chelating ligand of the formula (I) used.
- OAc is O 2 CCH 3 .
- Suitable solvents for the metal-catalyzed cross-coupling of chelating ligands of the formula (I) with organometallic reagents of the formula (III) are, for example, aliphatic ethers such as diethyl ether, dibutyl ether, methyl tert-butyl ether, tetrahydrofuran, dioxane and dimethoxyethane, aliphatic hydrocarbons such as pentane, hexane and the like, aromatic hydrocarbons such as benzene, toluene, xylenes and the like. In many cases, other solvents can be used, such as dimethylformamide, water, acetone and the like.
- protic solvents such as water, alcohols and their mixtures with aprotic solvents can be also be used, but only in the case of Suzuki reactions involving starting materials (I) where the bridging group B is not SiR 2 , GeR 2 , SiR 2 —SiR 2 , GeR 2 —GeR 2 , BR, BR—BR and the like, since these groups are labile in the presence of the transition-metal catalyst in protic solvents.
- the chelating ligand of the formula (I) together with a sufficient amount of solvent are placed in the reaction vessel under an inert atmosphere.
- the catalyst, an optional ligand and an optional base or nucleophilic aid agent are subsequently added followed by the addition of a solution of the organometallic compound of the formula (III) in a suitable solvent at room or lower ( ⁇ 78° C. to +10° C.) temperatures.
- the cross-coupling reaction can be carried out by vigorous stirring at room or elevated temperatures depending on the reaction under study, the reagents and the catalyst used. Addition of the reagents, catalyst and other additives can be performed in different orders. A person skilled in the art will choose an appropriate procedure depending on the reactivity and substitution of the individual reagents.
- Non-limiting preferred examples of the chelating ligands of the formula (II), where R is hydrocarbyl, substituted hydrocarbyl, halocarbyl, or substituted halocarbyl, which can be prepared according to the present invention include:
- a particular advantage of the present invention is that readily obtainable and inexpensive compounds of the formula (I) bearing chloroindenyl, bromoindenyl, chlorocyclopenta[b]thienyl, bromocyclopenta[b]thienyl fragments can be used as starting material, thus avoiding the necessity, as in the prior art, of first synthesizing the corresponding substituted indenes to then obtain the desired bridging ligands containing the respective hydrocarbyl, substituted hydrocarbyl, halocarbyl, or substituted halocarbyl substituted indenes and cyclopenta[b]thiophenes.
- the substituted chelating ligands of the formula (II) prepared according to the present invention can be used in all known applications of the chelating ligands, for example as intermediates for the preparation of transition metal complexes of importance for material chemistry, pharmacy, fine chemicals, organic light-emitting diodes (OLEDs), catalysis and the like.
- substituted chelating ligands of the formula (II) prepared according to the present invention can be advantageously used for the synthesis of metallocene complexes which are suitable for the polymerization of olefins, in particular ⁇ -olefins.
- substituted chelating ligands of the formula (II) are preferably used for the synthesis of chiral ansa-bisindenyl metallocenes and related complexes.
- the ansa-bisindenyl metallocenes and related complexes of the present invention contain a metal of Groups 4, 5 or 6, in particular Group 4, of the Periodic Table of the Elements, i.e. titanium, zirconium or hafnium.
- the metal is preferably zirconium or hafnium, most preferably zirconium.
- this invention relates to: 1.
- a process for preparing a chelating ligand of the formula (II) from a chelating ligand of the formula (I) via an sp 2 -sp 2 or sp 2 -sp 3 coupling reaction comprising contacting, optionally in the presence of a coupling catalyst, a chelating ligand of the formula (I) with an organometallic compound of the formula (II): wherein B is a bridging group that is bonded to L 1 and L 2 in formula (I) and to L 3 and L 4 in formula (II);
- L 1 is a substituted monocyclic or polycyclic ligand that comprises at least one chlorine, bromine, iodine, or sulfonate substituent, directly bonded to an sp 2 carbon atom of the ring structure of the ligand;
- L 2 is a monoanionic ligand; or L 2 may, independently, be defined as L 1 ;
- L 3 is the
- L 1 comprises at least one chlorine, bromine, or triflate, preferably at least one bromine or triflate, directly bonded to an sp 2 carbon atom of the ring structure of the ligand.
- L 1 is a substituted indenyl, a substituted heteroindenyl, a substituted fluorenyl, or a substituted heterofluorenyl ligand. 4.
- the coupling catalyst comprises poly(ethylene glycol)triphenylphosphin, polymer bound; dicyclohexylphenylphosphine, polymer-bound; (4-hydroxyphenyl)diphenylphosphine, polymer-bound; triphenylphosphine, polymer-supported; R-(+)-2,2′-bis(diphenylphosphino)-1,1′-binaphthalene, polymer-bound; or S-( ⁇ )-2,2′-bis(diphenylphosphino)-1,1′-binaphthalene, polymer bound. 5.
- L 2 is a substituted or unsubstituted monocyclic or polycyclic ligand, preferably L 2 is a substituted or unsubstituted cyclopentadienyl ligand, a substituted or unsubstituted heterocyclopentadienyl ligand, a substituted or unsubstituted indenyl ligand, a substituted or unsubstituted heteroindenyl ligand, a substituted or unsubstituted fluorenyl ligand, a substituted or unsubstituted heterofluorenyl ligand. 6.
- R 1 is a hydrocarbyl, substituted hydrocarbyl, halocarbyl, or substituted halocarbyl
- R 2 , R 3 , R 4 , and R 5′ are, independently, hydrogen, hydrocarbyl, substituted hydrocarbyl, halocarbyl, substituted halocarbyl, silylcarbyl, germylcarbyl radical or polar group as defined above; provided that all R 2 groups may be different and, optionally, adjacent R 2 , R 3 , R 4 , and R 5′ groups may also together form a cyclic aliphatic or aromatic ring system which may in turn be substituted and may contain heteroatoms; and provided further that R 2 , R 3 , and R 4 groups are attached to ring carbons; R 5′ groups are attached to heteroatoms; each Q, if present, is, independently, a Group 16 atom, a Group 15 atom, or boron, and preferably S, O, N, or P; when a Q is
- X 3 , X 4 , X 5 , and X 6 are independently selected from chlorine, bromine, and triflate, preferably from bromine and triflate.
- X 3 , X 4 , X 5 , and X 6 are independently selected from chlorine, bromine, and triflate, preferably from bromine and triflate.
- X 3 and X 4 are, independently, chlorine, bromine, or triflate, preferably bromine or triflate.
- M 1 is Li, Na, K, Rb, Cs, Be, Mg, Ca, Sr, Ba, B, Si, Sn, Zn, Cd or Hg.
- M 1 is B, Si, Sn, Zn, Cd or Hg.
- M 1 is B, Sn or Zn. 19.
- Hydrocarbon solvents such as benzene (Merck), toluene (Merck) and hexanes (Merck) and including benzene-d 6 for NMR measurements were typically distilled over CaH 2 , and were stored over Na/K alloy under an inert atmosphere; prior to use, the solvents were distilled from the Na/K alloy.
- Methylene chloride (Merck) and CCl 2 D 2 (Cambridge Isotope) for NMR measurements were distilled and stored over CaH 2 under an inert atmosphere; prior to use, the solvents were distilled from the CaH 2 .
- This toluene solution was treated with a catalytic amount of p TolSO 3 H (ca. 2 g) for 2 hours at reflux using a Dean-Stark head.
- the reaction was cooled to room temperature, washed with aqueous NaHCO 3 , dried over Na 2 SO 4 , and evaporated to dryness.
- the product was isolated by flash chromatography on Silica Gel 60 (40-63 ⁇ m, d 30 mm, l 300 mm; eluent: hexanes). Yield 38.7 g (87%) of white crystalline product.
- the aqueous layer was extracted with 4 ⁇ 200 ml of CH 2 Cl 2 .
- the combined organic fractions were washed with 1000 ml of the saturated aqueous Na 2 CO 3 , dried over K 2 CO 3 , passed through short column with Silica Gel 60 (40-63 ⁇ m, d 40 mm, l 50 mm), and evaporated to dryness.
- Fractional distillation gave white crystalline product, b.p. 128° C./0.8 mm Hg. Yield 185 g (94%).
- This extract was washed with the saturated aqueous Na 2 CO 3 , dried over K 2 CO 3 , and evaporated to dryness.
- 150 ml of toluene was added.
- This toluene solution was treated with a catalytic amount of p TolSO 3 H (ca. 0.2 g) for 10 min at reflux, cooled to room temperature, and, then, passed through a short Silica Gel 60 column (40-63 ⁇ m, d 20 mm, 150 mm). This column was additionally eluted with 300 ml of hexanes-methyl-tert-butyl ether mixture (10:1, vol.). The chromatographed product was evaporated to dryness.
- This toluene solution was treated with a catalytic amount of p TolSO 3 H (ca. 0.2 g) for 1 h at reflux, cooled to room temperature, and evaporated to dryness.
- the crude product was purified using flash chromatography on Silica Gel 60 (40-63 ⁇ m, d 40 mm, l 400 mm; eluent: hexanes). Yield 19.6 g (94%) of 4-bromo-6-isopropyl-2-methyl-1H-indene.
Abstract
wherein B is a bridging group that is bonded to L1 and L2 in formula (I) and to L3 and L4 in formula (II); L1 is a substituted monocyclic or polycyclic ligand that comprises at least one chlorine, bromine, iodine, or sulfonate substituent, directly bonded to an sp2 carbon atom of the ring structure of the ligand; L2 is a monoanionic ligand; or L2 may, independently, be defined as L1; L3 is the same group as L1, but said at least one chlorine, bromine, iodine, or sulfonate substituent is replaced with a hydrocarbyl, substituted hydrocarbyl, halocarbyl, or substituted halocarbyl fragment; L4 is the same group as L2, though, when L2 is defined as L1, L4 may be the same as L3 or L1; R1 is a hydrocarbyl, substituted hydrocarbyl, halocarbyl, or substituted halocarbyl; M1 is an element of group 1, 2, 12, 13 or 14 of the Periodic Table of the Elements; each X2, if present, is selected independently from the group consisting of halogen atoms, the hydroxyl group, alkoxy groups, aryloxy groups, mesylate, tosylate and triflate; r is 1, 2 or 3, and t is 0, 1 or 2, where r+t corresponds to the oxidation number of M1.
Description
- The present invention relates to a process for preparing substituted bridged indenyl and related ligands, to the substituted ligands prepared in this way and to their use in preparing metallocenes for olefin polymerization catalysts.
- Various processes and catalysts exist for the homopolymerization or copolymerization of olefins. For many applications, it is desirable for a polyolefin to have a high weight average molecular weight while having a relatively narrow molecular weight distribution. A high weight average molecular weight, when accompanied by a narrow molecular weight distribution, provides a polyolefin with high strength properties.
- Traditional Ziegler-Natta catalysts systems—a transition metal compound co-catalyzed by an aluminum alkyl—are typically capable of producing polyolefins having a high molecular weight, but with a broad molecular weight distribution.
- More recently a catalyst system has been developed wherein the transition metal compound has one or more cyclopentadienyl ring ligands (typically two)—such transition metal compound being referred to herein as a “metallocene”—which catalyzes the production of olefin monomers to polyolefins. Accordingly, titanocenes, zirconocenes and hafnocenes, have been utilized as the transition metal component in such “metallocene” containing catalyst system for the production of polyolefins and ethylene-alpha-olefin copolymers.
- Catalysts that produce isotactic polyolefins are disclosed in U.S. Pat. No. 4,794,096. This patent discloses a chiral, stereorigid metallocene catalyst which is activated by an alumoxane cocatalyst and which is reported to polymerize olefins to isotactic polyolefin forms. Alumoxane co-catalyzed metallocene structures which have been reported to polymerize alpha-olefins stereoregularly include the ethylene bridged bis-indenyl and bis-tetrahydroindenyl titanium and zirconium (IV) catalysts. Such catalyst systems were synthesized and studied in Wild et al., J. Organomet. Chem. 232, 233-47 (1982), and were later reported in Ewen and Kaminsky et al., mentioned above, to polymerize alpha-olefins stereoregularly. Further reported in West German Off. DE 3443087A1 (1986), but without giving experimental verification, is that the bridge length of such stereorigid metallocenes can vary from a C1 to C4 hydrocarbon and the metallocene rings can be simple or bi-cyclic but must be asymmetric. When substituted or unsubstituted indenyl or tetrahydroindenyl based, these metallocenes are bridged in the “1-position” of the (hydro)indenyl ring, and are of C2 symmetry. Generally speaking, it is the C2 symmetric structure (also referred to as the d/l-enantiomers or racemic complexes) that produces isotactic poly-alpha-olefins. An alternate form is the Cs symmetric or meso form that produces atactic poly-alpha-olefins.
- Thus, use of substituted bridged bis-indenyl and related ligands as starting materials makes it possible to obtain chiral ansa-metallocenes which are of great importance as transition metal components of active catalysts in the stereospecific polymerization of olefins. Variation of the ligand system, for example by means of substitution, enables the catalyst properties to be influenced in a targeted manner. This makes it possible to alter the polymer yield, the molecular weight distribution, the tacticity and the melting point of the polymers to the desired degree (Chem. Rev. 2000, vol. 100, no. 4; Metallocenes: Synthesis, Reactivity, Applications Ed. by A. Togni, R. L. Halterman.—Wiley-VCH, 1998). Bridged zirconocenes containing, as π ligands, indenyl radicals, which bear the bridge in position 1 and which preferably bear a hydrocarbon radical in position 2 and a hydrocarbon radical in position 4, have been found to be particularly highly active and stereoselective catalyst systems (European Patent Publication No. 0567970 A1; European Patent Publication No 0629632 A2). The ligand systems used for these highly active metallocenes are prepared from the corresponding indenes.
- A number of processes comprising an inexpensive coupling reaction have been described for the preparation of certain aryl- and alkyl-substituted indenes and indanones (International Patent Publication No. WO 98/40331; U.S. Pat. No. 5,789,634; International Patent Publication No. WO 03/084904 A1). However, the synthesis of aryl-, alkyl-, and alkenyl-substituted bridged indenyl and related ligands has not been studied so far, though this methodology could provide an attractive route for obtaining libraries of the substituted metal complexes. Also, in the case of bridged indenyl and related ligands with an SiR2 bridge, Suzuki coupling reactions in protic medium will result in cleavage of such allylic silicon bridging group [Metal-catalyzed cross coupling reactions by Diederich, F.; Stang, P. J., Eds.; Wiley-VCH, 1998].
- There is therefore a need for a simple and flexible process for preparing aryl-, alkyl-, and alkenyl-substituted bridged indenyl and related chelating ligands which are important intermediates for the preparation of active compounds and metallocene complexes.
- According to the invention, it has now been found that substituted bridged indenyl and related chelating ligands containing halogen and/or sulfonate as leaving groups can be converted in a simple manner into substituted bridged indenyl and related chelating ligands which contain hydrocarbyl, substituted hydrocarbyl, halocarbyl, or substituted halocarbyl substituents bound via sp2 or sp3 center and which can be further used for the preparation of active compounds and metallocene complexes.
- In one aspect, the present invention resides in a process for preparing a chelating ligand of the formula (II) from a chelating ligand of the formula (I) via an sp2-sp2 or sp2-sp3 coupling reaction with an organometallic compound of formula (III):
wherein
B is a bridging group that is bonded to L1 and L2 in formula (I) and to L3 and L4 in formula (II);
L1 is a substituted monocyclic or polycyclic ligand that comprises at least one chlorine, bromine, iodine, or sulfonate substituent, directly bonded to an sp2 carbon atom of the ring structure of the ligand;
L2 is a monoanionic ligand; or L2 may, independently, be defined as L1;
L3 is the same group as L1, but said at least one chlorine, bromine, iodine, or sulfonate substituent is replaced with a hydrocarbyl, substituted hydrocarbyl, halocarbyl, or substituted halocarbyl fragment;
L4 is the same group as L2, though, when L2 is defined as L1, L4 may be the same as L3 or L1;
R1 is a hydrocarbyl, substituted hydrocarbyl, halocarbyl, or substituted halocarbyl;
M1 is an element of Group 1, 2, 12, 13 or 14 of the Periodic Table of the Elements, preferably Li, Na, K, Rb, Cs, Be, Mg, Ca, Sr, Ba, B, Si, Sn, Zn, Cd or Hg, more preferably B, Si, Sn, Zn, Cd or Hg, and most preferably B, Sn or Zn;
each X2, if present, is selected independently from the group consisting of halogen atoms, the hydroxyl group, alkoxy groups, aryloxy groups, mesylate, tosylate and triflate, preferably from the group consisting of halogen atoms, the hydroxyl group, alkoxy and aryloxy;
r is 1, 2 or 3, and
t is 0, 1 or 2, where r+t corresponds to the oxidation number of M1. - Conveniently, L1 is a substituted indenyl, a substituted heteroindenyl, a substituted fluorenyl, or a substituted heterofluorenyl ligand.
- Conveniently, L2 is a substituted or unsubstituted monocyclic or polycyclic ligand, preferably a substituted or unsubstitued cyclopentadienyl ligand, a substituted or unsubstituted heterocyclopentadienyl ligand, a substituted or unsubstituted indenyl ligand, a substituted or unsubstituted heteroindenyl ligand, a substituted or unsubstituted fluorenyl ligand, a substituted or unsubstituted heterofluorenyl ligand.
- Preferably, L1 comprises at least one chlorine, bromine, or triflate directly bonded to an sp2 carbon atom of the ring structure of the ligand, and most preferably L1 comprises at least one bromine or triflate directly bonded to an sp2 carbon atom of the ring structure of the ligand.
- Ligands of formula (II) have been further used to obtain the respective metallocenes. The latter compounds, when combined with activators, readily polymerize various unsaturated monomers.
- Definitions
- As used herein, the numbering scheme for the Periodic Table Groups is the new notation as set out in C
HEMICAL AND ENGINEERING NEWS , 63(5), 27 (1985). Note however that in some of the formulae herein the capital letter “B” is used to indicate a bridge. It is not intended that such bridges be limited to boron, even if boron is one of the possible substituents. - As used herein, Me is methyl, t-Bu and tBu are tertiary butyl, iPr and iPr are isopropyl, Cy is cyclohexyl, and Ph is phenyl.
- The terms “hydrocarbyl radical,” “hydrocarbyl” and “hydrocarbyl group” are used interchangeably throughout this document. Likewise the terms “group”, “radical”, and “substituent” are also used interchangeably in this document. For purposes of this disclosure, “hydrocarbyl radical” is defined to be C1-C100 radicals, that may be linear, branched, or cyclic, and when cyclic, aromatic or non-aromatic, and include substituted hydrocarbyl radicals, halocarbyl radicals, and substituted halocarbyl radicals, silylcarbyl radicals, and germylcarbyl radicals as these terms are defined below.
- Substituted hydrocarbyl radicals are radicals in which at least one hydrogen atom has been substituted with at least one functional group such as NR*2, OR*, SeR*, TeR*, PR*2, AsR*2, SbR*2, SR*, BR*2, SiR*3, GeR*3, SnR*3, PbR*3 and the like or where at least one non-hydrocarbon atom or group has been inserted within the hydrocarbyl radical, such as —O—, —S—, —Se—, —Te—, —N(R*)—, ═N—, —P(R*)—, ═P—, —As(R*)—, ═As—, —Sb(R*)—, ═Sb—, —B(R*)—, ═B—, —Si(R*)2—, —Ge(R*)2—, —Sn(R*)2—, —Pb(R*)2— and the like, where R* is independently a hydrocarbyl or halocarbyl radical, and two or more R* may join together to form a substituted or unsubstituted saturated, partially unsaturated or aromatic cyclic or polycyclic ring structure.
- Halocarbyl radicals are radicals in which one or more hydrocarbyl hydrogen atoms have been substituted with at least one halogen (e.g. F, Cl, Br, I) or halogen-containing group (e.g. CF3).
- Substituted halocarbyl radicals are radicals in which at least one halocarbyl hydrogen or halogen atom has been substituted with at least one functional group such as NR*2, OR*, SeR*, TeR*, PR*2, AsR*2, SbR*2, SR*, BR*2, SiR*3, GeR*3, SnR*3, PbR*3 and the like or where at least one non-carbon atom or group has been inserted within the halocarbyl radical such as —O—, —S—, —Se—, —Te—, —N(R*)—, ═N—, —P(R*)—, ═P—, —As(R*)—, ═As—, —Sb(R*)—, ═Sb—, —B(R*)—, ═B—, —Si(R*)2—, —Ge(R*)2—, —Sn(R*)2—, —Pb(R*)2— and the like, where R* is independently a hydrocarbyl or halocarbyl radical provided that at least one halogen atom remains on the original halocarbyl radical. Additionally, two or more R* may join together to form a substituted or unsubstituted saturated, partially unsaturated or aromatic cyclic or polycyclic ring structure.
- Silylcarbyl radicals (also called silylcarbyls) are groups in which the silyl functionality is bonded directly to the indicated atom or atoms. Examples include SiH3, SiH2R*, SiHR*2, SiR*3, SiH2(OR*), SiH(OR*)2, Si(OR*)3, SiH2(NR*2), SiH(NR*2)2, Si(NR*2)3, and the like where R* is independently a hydrocarbyl or halocarbyl radical and two or more R* may join together to form a substituted or unsubstituted saturated, partially unsaturated or aromatic cyclic or polycyclic ring structure.
- Germylcarbyl radicals (also called germylcarbyls) are groups in which the germyl functionality is bonded directly to the indicated atom or atoms. Examples include GeH3, GeH2R*, GeHR*2, GeR5 3, GeH2(OR*), GeH(OR*)2, Ge(OR*)3, GeH2(NR*2), GeH(NR*2)2, Ge(NR*2)3, and the like where R* is independently a hydrocarbyl or halocarbyl radical and two or more R* may join together to form a substituted or unsubstituted saturated, partially unsaturated or aromatic cyclic or polycyclic ring structure.
- Polar radicals, functional groups, or polar groups are groups in which the heteroatom functionality is bonded directly to the indicated atom or atoms. They include heteroatoms of groups 1-17 of the periodic table either alone or connected to other elements by covalent or other interactions such as ionic, van der Waals forces, or hydrogen bonding. Examples of functional groups include carboxylic acid, acid halide, carboxylic ester, carboxylic salt, carboxylic anhydride, aldehyde and their chalcogen (Group 14) analogues, alcohol and phenol, ether, peroxide and hydroperoxide, carboxylic amide, hydrazide and imide, amidine and other nitrogen analogues of amides, nitrile, amine and imine, azo, nitro, other nitrogen compounds, sulfur acids, selenium acids, thiols, sulfides, sulfoxides, sulfones, phosphines, phosphates, other phosphorus compounds, silanes, boranes, borates, alanes, aluminates. Functional groups may also be taken broadly to include organic polymer supports or inorganic support material such as alumina, and silica. Preferred examples of polar groups include NR*2, OR*, SeR*, TeR*, PR*2, AsR*2, SbR*2, SR*, BR*2, SnR*3, PbR*3 and the like where R* is independently a hydrocarbyl, substituted hydrocarbyl, halocarbyl or substituted halocarbyl radical as defined above and two R* may join together to form a substituted or unsubstituted saturated, partially unsaturated or aromatic cyclic or polycyclic ring structure.
- Sulfonate radical is a group in which hydrocarbyl, substituted hydrocarbyl, halocarbyl, or substituted halocarbyl is bonded to sulfur in —O—S(═O)2 group. Examples include SO3Me (mesylate), SO3(4-tosyl) (tosylate), SO3CF3 (triflate), SO3(n-C4F9) (nonaflate) and the like.
- In using the terms “substituted or unsubstituted monocyclic or polycyclic ligand”, “substituted or unsubstituted cyclopentadienyl ligand”, “substituted or unsubstituted heterocyclopentadienyl ligand”, “substituted or unsubstituted indenyl ligand”, “substituted or unsubstituted heteroindenyl ligand”, “substituted or unsubstituted fluorenyl ligand”, “substituted or unsubstituted heterofluorenyl ligand”, “substituted or unsubstituted pentadienyl ligand”, “substituted or unsubstituted allyl ligand”, and “substituted or unsubstituted boratabenzene ligand”, the substitution to the aforementioned ligand may be hydrocarbyl, substituted hydrocarbyl, halocarbyl, substituted halocarbyl, silylcarbyl, or germylcarbyl.
- In some embodiments, the hydrocarbyl radical is independently selected from methyl, ethyl, ethenyl and isomers of propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl, eicosyl, heneicosyl, docosyl, tricosyl, tetracosyl, pentacosyl, hexacosyl, heptacosyl, octacosyl, nonacosyl, triacontyl, propenyl, butenyl, pentenyl, hexenyl, heptenyl, octenyl, nonenyl, decenyl, undecenyl, dodecenyl, tridecenyl, tetradecenyl, pentadecenyl, hexadecenyl, heptadecenyl, octadecenyl, nonadecenyl, eicosenyl, heneicosenyl, docosenyl, tricosenyl, tetracosenyl, pentacosenyl, hexacosenyl, heptacosenyl, octacosenyl, nonacosenyl, triacontenyl, propynyl, butynyl, pentynyl, hexynyl, heptynyl, octynyl, nonynyl, decynyl, undecynyl, dodecynyl, tridecynyl, tetradecynyl, pentadecynyl, hexadecynyl, heptadecynyl, octadecynyl, nonadecynyl, eicosynyl, heneicosynyl, docosynyl, tricosynyl, tetracosynyl, pentacosynyl, hexacosynyl, heptacosynyl, octacosynyl, nonacosynyl, triacontynyl, butadienyl, pentadienyl, hexadienyl, heptadienyl, octadienyl, nonadienyl, and decadienyl. Also included are isomers of saturated, partially unsaturated and aromatic cyclic and polycyclic structures wherein the radical may additionally be subjected to the types of substitutions described above. Examples include phenyl, methylphenyl, dimethylphenyl, ethylphenyl, diethylphenyl, propylphenyl, dipropylphenyl, benzyl, methylbenzyl, naphthyl, anthracenyl, cyclopentyl, cyclopentenyl, cyclohexyl, cyclohexenyl, methylcyclohexyl, cycloheptyl, cycloheptenyl, norbornyl, norbornenyl, adamantyl and the like. For this disclosure, when a radical is listed, it indicates that radical type and all other radicals formed when that radical type is subjected to the substitutions defined above. Alkyl, alkenyl and alkynyl radicals listed include all isomers including where appropriate cyclic isomers, for example, butyl includes n-butyl, 2-methylpropyl, 1-methylpropyl, tert-butyl, and cyclobutyl (and analogous substituted cyclopropyls); pentyl includes n-pentyl, cyclopentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 1-ethylpropyl, and neopentyl (and analogous substituted cyclobutyls and cyclopropyls); butenyl includes E and Z forms of 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 1-methyl-2-propenyl, 2-methyl-1-propenyl and 2-methyl-2-propenyl (and cyclobutenyls and cyclopropenyls). Cyclic compound having substitutions include all isomer forms, for example, methylphenyl would include ortho-methylphenyl, meta-methylphenyl and para-methylphenyl; dimethylphenyl would include 2,3-dimethylphenyl, 2,4-dimethylphenyl, 2,5-dimethylphenyl, 2,6-diphenylmethyl, 3,4-dimethylphenyl, and 3,5-dimethylphenyl.
- For nomenclature purposes, the following numbering schemes are used for cyclopentadienyl, indenyl, fluorenyl, and cyclopentanaphthyl (also termed benzindenyl). It should be noted that indenyl can be considered ascyclopentadienyl fused with a benzene ring. Analogously, fluorenyl can be considered a cyclopentadienyl with two phenyl rings fused onto the cyclopentadienyl ring. Each structure below is drawn and named as an anion.
- A similar numbering and nomenclature scheme is used for heterocyclopentadienyls, heterophenyls, heteropentalenyls, heterocyclopentapentalenyls, heteroindenyls, heterofluorenyls, heterocyclopentanaphthyls, heterocyclopentaindenyls, heterobenzocyclopentaindenyls, and the like, as illustrated below. Each structure is drawn and named as an anion.
-
- Further non-limiting examples of heterocyclopentadienyls include 1,3-diazacyclopentadienyl, 1,3-diphosphacyclopentadienyl, 1,3-diarsacyclopentadienyl, 1,3-distibacyclopentadienyl, 1,3-diboracyclopentadienyl, 1,3-azaphosphacyclopentadienyl, 1,3-azaarsacylcopentadienyl, 1,3-azastibacyclopentadienyl, 1,3-azaboracyclopentadienyl, 1,3-arsaphosphacyclopentadienyl, 1,3-arsastibacyclopentadienyl, 1,3-arsaboracyclopentadienyl, 1,3-boraphosphacyclopentadienyl, 1,3-borastibacylcopentadienyl, 1,3-phosphastibacyclopentadienyl, 1,2-diazacyclopentadienyl, 1,2-diphosphacyclopentadienyl, 1,2-diarsacyclopentadienyl, 1,2-distibacyclopentadienyl, 1,2-diboracyclopentadienyl, 1,2-azaphosphacyclopentadienyl, 1,2-azaarsacylcopentadienyl, 1,2-azastibacyclopentadienyl, 1,2-azaboracyclopentadienyl, 1,2-arsaphosphacyclopentadienyl, 1,2-arsastibacyclopentadienyl, 1,2-arsaboracyclopentadienyl, 1,2-boraphosphacyclopentadienyl, 1,2-borastibacylcopentadienyl, 1,2-phosphastibacyclopentadienyl, 3-dihydrocarbylamino-1,3-azaborollide, 2-dihydrocarbylamino-1,2-oxaborollide, 2-dihydrocarbylamino-1,2-thiaborollide, 3-hydrocarbyloxy-1,3-azaborollide, 2-hydrocarbyloxy-1,2-oxaborollide, 2-hydrocarbyloxy-1,2-thiaborollide, 3-hydrocarbyl-1,3-azaborollide, 2-hydrocarbyl-1,2-oxaborollide, and 2-hydrocarbyl-1,2-thiaborollide, where hydrocarbyl is a “hydrocarbyl radical” as previously defined.
-
- Further non-limiting examples of heterophenyls include 1-dihydrocarbylaminoboratabenzene, 4-dihydrocarbylamino-1,4-phosphaboratabenzene, 2-dihydrocarbylamino-1,2-azaboratabenzene, 1-hydrocarbyloxyboratabenzene, 4-hydrocarbyloxy-1,4-phosphaboratabenzene, 2-hydrocarbyloxy-1,2-azaboratabenzene, 1-hydrocarbylboratabenzene, 4-hydrocarbyl-1,4-phosphaboratabenzene, and 2-hydrocarbyl-1,2-azaboratabenzene, where hydrocarbyl is a “hydrocarbyl radical” as previously defined.
-
- Further non-limiting examples of heteropentalenyls include cyclopenta[b]selenophenyl, cyclopenta[c]selenophenyl, cyclopenta[b]tellurophenyl, cyclopenta[c]tellurophenyl, 1-hydrocarbylcyclopenta[b]arsolyl, 2-hydrocarbylcyclopenta[c]arsolyl, 1-hydrocarbylcyclopenta[b]stibolyl, 2-hydrocarbylcyclopenta[c]stibolyl, 1-hydrocarbylcyclopenta[b]pyrrolyl, 2-hydrocarbylcyclopenta[c]pyrrolyl, 1-hydrocarbylcyclopenta[b]phospholyl, and 2-hydrocarbylcyclopenta[c]phospholyl, where hydrocarbyl is a “hydrocarbyl radical” as previously defined.
- Non-limiting examples of heterocylopentapentalenyls include the following, where Z and Q independently represent the heteroatoms O, S, Se, or Te, or heteroatom groups, NR**, PR**, AsR**, or SbR** where R** is hydrogen, or a hydrocarbyl, substituted hydrocarbyl, halocarbyl, substituted halocarbyl, silylcarbyl, or germylcarbyl substituent.
- Further non-limiting examples of heteroindenyls include cyclopenta[b]arsinyl, cyclopenta[c]arsinyl, cyclopenta[b]stibinyl, cyclopenta[c]stibinyl, 3-dihydrocarbylamino-1,3-benzothiaborollide, 2dihydrocarbylamino-1,2-benzothiaborollide, 3-hydrocarbyloxy-1,3-benzothiaborollide, 2-hydrocarbyloxy-1,2-benzothiaborollide, 3-hydrocarbyl-1,3-benzothiaborollide, and 2-hydrocarbyl-1,2-benzothiaborollide, where hydrocarbyl is a “hydrocarbyl radical” as previously defined.
-
-
- Further non-limiting examples of heterocyclopentanaphthyls include cyclopenta[g]phosphinolyl, cyclopenta[g]isophosphinolyl, cyclopenta[g]arsinolyl, and cyclopenta[g]isoarsinolyl.
-
- Further non-limiting examples of heterocyclopentaindenyls include 1-hydrocarboncylcyclopenta[f]phosphindolyl, 2-hydrocarboncylcyclopenta[f]isophosphindolyl, 1-hydrocarbylcyclopenta[f]arsindolyl, 2-hydrocarbylcyclopenta[f]isoarsindolyl, indeno[5,6-b]selenophenyl, indeno[5,6-b]tellurophenyl, indeno[5,6-c]selenophenyl, indeno[5,6-c]tellurophenyl, 2-hydrocarbylcylcyclopenta[f]isoindolyl, and 1-hydrocarbylcyclopenta[f]indolyl, where hydrocarbyl is a “hydrocarbyl radical” as previously defined.
-
- Further non-limiting examples of heterobenzocyclopentaindenyls include 5-hydrocarbylindeno[1,2-b]indolyl and 5-hydrocarbylindeno[2,1-b]indolyl, where hydrocarbyl is a “hydrocarbyl radical” as previously defined.
- The term “arene” ligand is used herein to mean an unsaturated cyclic hydrocarbyl ligand that can consist of one ring, or two or more fused or catenated rings.
- As used herein, the term “monocyclic ligand” is intended to mean any substituted or unsubstituted C5 to C100 monoanionic aromatic five-membered or six-membered single ring structure composed of ring carbon atoms, either alone or in combination with one or more ring heteroatoms. In contrast, the term “monocyclic arene ligand” is used herein to mean a substituted or unsubstituted monoanionic C5 to C100 hydrocarbyl ligand that contains an aromatic five-membered single hydrocarbyl ring structure (also referred to as a cyclopentadienyl ring).
- As used herein, the term “polycyclic ligand” is intended to mean any substituted or unsubstituted C5 to C103 monoanionic partially unsaturated or aromatic multiple fused ring structure containing at least one aromatic five-membered ring structure, said ligand composed of ring carbon atoms, either alone or in combination with one or more ring heteroatoms. In contrast, the term “polycyclic arenyl ligand” is used herein to mean a substituted or unsubstituted monoanionic C8 to C103 hydrocarbyl ligand that contains an aromatic five-membered hydrocarbyl ring (also referred to as a cyclopentadienyl ring) that is fused to one or two partially unsaturated, or aromatic hydrocarbyl ring structures which may be fused to additional saturated, partially unsaturated, or aromatic hydrocarbyl rings.
- Monocyclic ligands include substituted or unsubstituted heterocyclopentadienyls and heterophenyls. Monocyclic arenyl ligands include substituted or unsubstituted cyclopentadienyls. Polycyclic ligands include substituted or unsubstituted, partially unsaturated or aromatic heteroindenyls, heteropentalenyls, heterocyclopentapentalenyls, heterofluorenyls, heterocyclopentanaphthyls, heterocyclopentaindenyls, and heterobenzocyclopentaindenyls. Polycyclic arenyl ligands include substituted or unsubstituted, partially unsaturated or aromatic indenyls, fluorenyls, and cyclopentanaphthyls.
- Non-limiting examples of polycyclic arene ligands, named also as monoanionic ligands, include indenyl, 4,5-dihydroindenyl, 4,7-dihydroindenyl, 4,5,6,7-tetrahydroindenyl, fluorenyl, 1,2-dihydrotetrahydrofluorenyl, 1,4-dihydrotetrahydrofluorenyl, 3,4-dihydrotetrahydrofluorenyl, 1,2,3,4-tetrahydrofluorenyl, 1,2,5,6-tetrahydrofluorenyl, 1,2,7,8-tetrahydrofluorenyl, 3,4,5,6-tetrahydrofluorenyl, 1,4,5,8-tetrahydrofluorenyl, 1,2,3,4,5,6,7,8-octahydrofluorenyl, cyclopenta[b]naphthyl, 4,4a-dihydrocyclopenta[b]naphthyl, 5,6-dihydrocyclopenta[b]naphthyl, 5,8-dihydrocyclopenta[b]naphthyl, 4,9-dihydrocyclopenta[b]naphthyl, 4,4a,5,6-tetrahydrocyclopenta[b]naphthyl, 4,5,8,9-tetrahydrocyclopenta[b]naphthyl, 4,4a,7,8-tetrahydrocyclopenta[b]naphthyl, 4,4a,8a,9-tetrahydrocyclopenta[b]naphthyl, 5,6,7,8-tetrahydrocyclopenta[b]naphthyl, 4,4a,5,8-tetrahydrocyclopenta[b]naphthyl, 4,5,6,9-tetrahydrocyclopenta[b]naphthyl, 4,6,7,8-tetrahydrocyclopenta[b]naphthyl, 4,6,7,9-tetrahydrocyclopenta[b]naphthyl, 4,4a,5,9-tetrahydrocyclopenta[b]naphthyl, 4,4a,5,6,7,8-hexahydrocyclopenta[b]naphthyl, 4,4a,5,6,8a,9-hexahydrocyclopenta[b]naphthyl, 4,4a,5,8,8a,9-hexahydrocyclopenta[b]naphthyl, 4,5,6,7,8,9-hexahydrocyclopenta[b]naphthyl, 4,4a,5,6,7,9-hexahydrocyclopenta[b]naphthyl, 4,4a,5,6,7,8,8a,9-octahydrocyclopenta[b]naphthyl, cyclopenta[a]naphthyl, 4,5-dihydrocyclopenta[a]naphthyl, 6,7-dihydrocyclopenta[a]naphthyl, 8,9-dihydrocyclopenta[a]naphthyl, 5a,9a-dihydrocyclopenta[a]naphthyl, 6,9-dihydrocyclopenta[a]naphthyl, 7,9a-dihydrocyclopenta[a]naphthyl, 4,9a-dihydrocyclopenta[a]naphthyl, 5a,8-dihydrocyclopenta[a]naphthyl, 4,5,5a,9a-tetrahydrocyclopenta[a]naphthyl, 4,5,6,7-tetrahydrocyclopenta[a]naphthyl, 4,5,8,9-tetrahydrocyclopenta[a]naphthyl, 5a,6,7,9a-tetrahydrocyclopenta[a]naphthyl, 6,7,8,9-tetrahydrocyclopenta[a]naphthyl, 5a,8,9,9a-tetrahydrocyclopenta[a]naphthyl, 4,5,7,9a-tetrahydrocyclopenta[a]naphthyl, 5a,6,7,9a-tetrahydrocyclopenta[a]naphthyl, 7,8,9,9a-tetrahydrocyclopenta[a]naphthyl, 4,6,7,9a-tetrahydrocyclopenta[a]naphthyl, 4,8,9,9a-tetrahydrocyclopenta[a]naphthyl, 4,5,6,9-tetrahydrocyclopenta[a]naphthyl, 4,5,5a,8-tetrahydrocyclopenta[a]naphthyl, 5a,6,7,8-tetrahydrocyclopenta[a]naphthyl, 5a,6,9,9a-tetrahydrocyclopenta[a]naphthyl, 5a,6,7,8,9,9a-hexahydrocyclopenta[a]naphthyl, 4,6,7,8,9,9a-hexahydrocyclopenta[a]naphthyl, 4,5,7,8,9,9a-hexahydrocyclopenta[a]naphthyl, 4,5,5a,8,9,9a-hexahydrocyclopenta[a]naphthyl, 4,5,5a,6,9,9a-hexahydrocyclopenta[a]naphthyl, 4,5,5a,6,7,9a-hexahydrocyclopenta[a]naphthyl, 4,5,5a,6,7,8-hexahydrocyclopenta[a]naphthyl, 4,5,6,7,8,9-hexahydrocyclopenta[a]naphthyl, 4,5,5a,6,7,8,9,9a-hexahydrocyclopenta[a]naphthyl, 4,5,5a,6,7,8,9,9a-octahydrocyclopenta[a]naphthyl, 5,6-trimethyleneindenyl, 4,5-trimethyleneindenyl, 5,6-pentamethyleneindenyl, 4,5-pentamethyleneindenyl, 5,6-hexamethyleneindenyl, 4,5-hexamethyleneindenyl, 5,6-heptamethyleneindenyl, 4,5-heptamethyleneindenyl, 5,6-octamethyleneindenyl, 4,5-octamethyleneindenyl, 5,6-nonamethyleneindenyl, 4,5-nonamethyleneindenyl, 5,6-decamethyleneindenyl, 4,5-decamethyleneindenyl, 5,6-undecamethyleneindenyl, 4,5-undecamethyleneindenyl, 5,6-dodecamethyleneindenyl, 4,5-dodecamethyleneindenyl, 5,6-tridecamethyleneindenyl, 4,5-tridecamethyleneindenyl, 5,6-tetradecamethyleneindenyl, 4,5-tetradecamethyleneindenyl, 5,6-pentadecamethyleneindenyl, 4,5-pentadecamethyleneindenyl, 5,6-hexadecamethyleneindenyl, 4,5-hexadecamethyleneindenyl, 5,6-heptadecamethyleneindenyl, 4,5-heptadecamethyleneindenyl, 5,6-octadecamethyleneindenyl, 4,5-octadecamethyleneindenyl, 5,6-nonadecamethyleneindenyl, 4,5-nonadecamethyleneindenyl, 5,6-eicosamethyleneindenyl, 4,5-eicosamethyleneindenyl, (6Z,8Z,10Z)-cycloocta[e]indenyl, (5Z,7Z,9Z)-cycloocta[f]indenyl, (5E,7Z,9E,11Z,13E)-cyclododeca[f]indenyl, (6E,8Z,10E,12Z,14E)-cyclododeca[e]indenyl, benz[a]fluorenyl, benz[b]fluorenyl, benz[c]fluorenyl, naphth[2,3-a]fluorenyl, naphth[2,3-b]fluorenyl, naphth[2,3-c]fluorenyl, naphth[1,2-a]fluorenyl, naphth[1,2-b]fluorenyl, naphth[1,2-c]fluorenyl, 2,3-tetramethylenefluorenyl, 1,2-tetramethylenefluorenyl, 3,4-tetramethylenefluorenyl, 2,3-trimethylenefluorenyl, 1,2-trimethylenefluorenyl, 3,4-trimethylenefluorenyl, 2,3-pentamethylenefluorenyl, 1,2-pentamethylenefluorenyl, 3,4-pentamethylenefluorenyl, 2,3-hexamethylenefluorenyl, 1,2-hexamethylenefluorenyl, 3,4-hexamethylenefluorenyl, 2,3-heptamethylenefluorenyl, 1,2-heptamethylenefluorenyl, 3,4-heptamethylenefluorenyl, 2,3-octamethylenefluorenyl, 1,2-octamethylenefluorenyl, 3,4-octamethylenefluorenyl, 2,3-nonamethylenefluorenyl, 1,2-nonamethylenefluorenyl, 3,4-nonamethylenefluorenyl, 2,3-decamethylenefluorenyl, 1,2-decamethylenefluorenyl, 3,4-decamethylenefluorenyl, 2,3-undecamethylenefluorenyl, 1,2-undecamethylenefluorenyl, 3,4-undecamethylenefluorenyl, 2,3-dodecamethylenefluorenyl, 1,2-dodecamethylenefluorenyl, 3,4-dodecamethylenefluorenyl, 2,3-tetramethylene-6,7-tetramethylenefluorenyl, 1,2-tetramethylene-7,8-tetramethylenefluorenyl, 3,4-tetramethylene-5,6-tetramethylenefluorenyl, bis-benz[2,3;6,7]fluorenyl, bis-benz[2,3;5,6]fluorenyl, bis-benz[1,2;7,8]fluorenyl, bis-benz[1,2;5,6]fluorenyl, bis-benz[1,2;6,7]fluorenyl, bis-benz[1,2;7,8]fluorenyl, and bis-benz[3,4;5,6]fluorenyl.
- Partially hydrogenated polycyclic arene ligands retain the numbering scheme of the parent polycyclic arene ligand, namely the numbering schemes defined for indenyl, fluorenyl, cyclopenta[b]naphthyl, and cyclopenta[a]naphthyl ligands.
- A “ring heteroatom” is a heteroatom that is within a cyclic ring structure. A “heteroatom substituent” is a heteroatom containing group that is directly bonded to a ring structure through the heteroatom. The terms “ring heteroatom” and “heteroatom substituent” are illustrated below where Z is a heteroatom group preferably S, O, Se, Te, N—R′, P—R′, As—R′, Sb—R′ or B—R′ and each R1 is independently a hydrocarbyl, substituted hydrocarbyl, halocarbyl or substituted halocarbyl radical as defined above and two R1 may join together to form a substituted or unsubstituted saturated, partially unsaturated or aromatic cyclic or polycyclic ring structure. If R′ is bonded to boron, R1 can additionally be a Group 15 or Group 16 group where the heteroatom is directly bonded to boron and R1 is then preferably an O—R″ group or an N—R12 group, where each R″ is independently a hydrocarbyl, substituted hydrocarbyl, halocarbyl or substituted halocarbyl radical as defined above and two R″ may join together to form a substituted or unsubstituted saturated, partially unsaturated or aromatic cyclic or polycyclic ring structure.
- A “ring carbon atom” is a carbon atom that is part of a cyclic ring structure. By this definition, an indenyl fragment has nine ring carbon atoms.
- A “bondable ring position” is a ring position that is capable of bearing a substituent or bridging substituent. For example, cyclopenta[b]thienyl has five bondable ring positions (at the carbon atoms) and one non-bondable ring position (the sulfur atom); cyclopenta[b]pyrrolyl has six bondable ring positions (at the carbon atoms and at the nitrogen atom).
- In the context of this document, “homopolymerization” would produce a polymer made from one monomer. For example, homopolymerization of propylene would produce homopolypropylene. Homopolymerization of ethylene would produce homopolyethylene. Likewise, “copolymerization” would produce polymers with more than one monomer type. For example, ethylene copolymers include polymers of ethylene with α-olefins, cyclic olefins and diolefins, vinylaromatic olefins, α-olefinic diolefins, substituted α-olefins, and/or acetylenically unsaturated monomers. Non-limiting examples of α-olefins include ethylene, propylene, 1-butene, 1-pentene, 1-hexene, 1-heptene, 1-octene, 1-nonene, 1-decene, 1-undecene 1-dodecene, 1-tridecene, 1-tetradecene, 1-pentadecene, 1-hexadecene, 1-heptadecene, 1-octadecene, 1-nonadecene, 1-eicosene, 1-heneicosene, 1-docosene, 1-tricosene, 1-tetracosene, 1-pentacosene, 1-hexacosene, 1-heptacosene, 1-octacosene, 1-nonacosene, 1-triacontene, 4-methyl-1-pentene, 3-methyl-1-pentene, 5-methyl-1-nonene, 3,5,5-trimethyl-1-hexene, vinylcyclohexane, and vinylnorbornane. Non-limiting examples of cyclic olefins and diolefins include cyclobutene, cyclopentene, cyclohexene, cycloheptene, cyclooctene, cyclononene, cyclodecene, norbornene, 4-methylnorbornene, 2-methylcyclopentene, 4-methylcyclopentene, vinylcyclohexane, norbornadiene, dicyclopentadiene, 5-ethylidene-2-norbornene, vinylcyclohexene, 5-vinyl-2-norbornene, 1,3-divinylcyclopentane, 1,2-divinylcyclohexane, 1,3-divinylcyclohexane, 1,4-divinylcyclohexane, 1,5-divinylcyclooctane, 1-allyl-4-vinylcyclohexane, 1,4-diallylcyclohexane, 1-allyl-5-vinylcyclooctane, and 1,5-diallylcyclooctane. Non-limiting examples of vinylaromatic olefins include styrene, para-methylstyrene, para-t-butylstyrene, vinylnaphthylene, vinyltoluene, and divinylbenzene. Non-limiting examples of α-olefinic dienes include 1,4-hexadiene, 1,5-hexadiene, 1,5-heptadiene, 1,6-heptadiene, 6-methyl-1,6-heptadiene, 1,7-octadiene, 7-methyl-1,7-octadiene, 1,9-decadiene, 1,11-dodecene, 1,13-tetradecene and 9-methyl-1,9-decadiene. Substituted α-olefins (also called functional group containing α-olefins) include those containing at least one non-carbon Group 13 to 17 atom bound to a carbon atom of the substituted α-olefin where such substitution if silicon may be adjacent to the double bond or terminal to the double bond, or anywhere in between, and where inclusion of non-carbon and non-silicon atoms such as for example B, O, S, Se, Te, N, P, Ge, Sn, Pb, As, F, Cl, Br, or I, are contemplated, where such non-carbon or non-silicon moieties are sufficiently far removed from the double bond so as not to interfere with the coordination polymerization reaction with the catalyst and so to retain the generally hydrocarbyl characteristic. By sufficiently far removed from the double bond we intend that the number of carbon atoms, or the number of carbon and silicon atoms, separating the double bond and the non-carbon or non-silicon moiety is preferably 6 or greater, e.g. 7, or 8, or 9, or 10, or 11, or 12, or 13, or 14 or more. The number of such carbon atoms, or carbon and silicon atoms, is counted from immediately adjacent to the double bond to immediately adjacent to the non-carbon or non-silicon moiety. Examples include 8,8,8-trifluoro-1-octene, 8-methoxyoct-1-ene, 8-methylsulfanyloct-1-ene, 8-dimethylaminooct-1-ene, or combinations thereof. The use of functional group-containing α-olefins where the functional group is closer to the double bond is also within the scope of embodiments of the invention when such olefins may be incorporated in the same manner as are their α-olefin analogs. See, “Metallocene Catalysts and Borane Reagents in The Block/Graft Reactions of Polyolefins”, T. C. Chung, et al, Polym. Mater. Sci. Eng., v. 73, p. 463 (1995), and the masked α-olefin monomers of U.S. Pat. No. 5,153,282. Such monomers permit the preparation of both functional-group containing copolymers capable of subsequent derivatization, and of functional macromers which may be used as graft and block type polymeric segments. Copolymerization can also incorporate α-olefinic macromonomers of up to 2000 mer units.
- For purposes of this disclosure, the term oligomer refers to compositions having 2-75 mer units and the term polymer refers to compositions having 76 or more mer units. A mer is defined as a unit of an oligomer or polymer that originally corresponded to the monomer(s) used in the oligomerization or polymerization reaction. For example, the mer of polyethylene would be ethylene.
- The term “catalyst system” is defined to mean a catalyst precursor/activator pair. When “catalyst system” is used to describe such a pair before activation, it means the unactivated catalyst (precatalyst) together with an activator and, optionally, a co-activator. When it is used to describe such a pair after activation, it means the activated catalyst and the activator or other charge-balancing moiety.
- The transition metal compound may be neutral as in a precatalyst, or a charged species with a counter ion as in an activated catalyst system.
- Catalyst precursor is also often referred to as precatalyst, catalyst, catalyst compound, catalyst precursor, transition metal compound or transition metal complex. These words are used interchangeably. Activator and cocatalyst are also used interchangeably. A scavenger is a compound that is typically added to facilitate oligomerization or polymerization by scavenging impurities. Some scavengers may also act as activators and may be referred to as co-activators. A co-activator, that is not a scavenger, may also be used in conjunction with an activator in order to form an active catalyst. In some embodiments a co-activator can be pre-mixed with the transition metal compound to form an alkylated transition metal compound, also referred to as an alkylated invention compound.
- Noncoordinating anion (NCA) is defined to mean an anion either that does not coordinate to the catalyst metal cation or that does coordinate to the metal cation, but only weakly. An NCA coordinates weakly enough that a neutral Lewis base, such as an olefinically or acetylenically unsaturated monomer can displace it from the catalyst center. Any metal or metalloid that can form a compatible, weakly coordinating complex may be used or contained in the noncoordinating anion. Suitable metals include, but are not limited to, aluminum, gold, and platinum. Suitable metalloids include, but are not limited to, boron, aluminum, phosphorus, and silicon.
- A stoichiometric activator can be either neutral or ionic. The terms ionic activator, and stoichiometric ionic activator can be used interchangeably. Likewise, the terms neutral stoichiometric activator, and Lewis acid activator can be used interchangeably.
- The chelating ligands according to the invention can be used to synthesize the respective transition metal derivatives of importance as catalyst components for the production of polymers or oligomers, including homopolymers, such as homopolyethylene or homopolypropylene, copolymers of ethylene with other olefins including alpha-olefins, and copolymers of propylene with other olefins including alpha-olefins.
- In a first embodiment, the invention provides a process for preparing a chelating ligand of the formula (II) from a chelating ligand of the formula (I) via an sp2-sp2 or sp2-sp3 coupling reaction with an organometallic compound of formula (III):
wherein
B is a bridging group that is bonded to L1 and L2 in formula (I) and to L3 and L4 in formula (II);
L1 is a substituted monocyclic or polycyclic ligand that comprises at least one chlorine, bromine, iodine, or sulfonate substituent, directly bonded to an sp2 carbon atom of the ring structure of the ligand;
L2 is a monoanionic ligand; or L2 may, independently, be defined as L1;
L3 is the same group as L1, but said at least one chlorine, bromine, iodine, or sulfonate substituent is replaced with a hydrocarbyl, substituted hydrocarbyl, halocarbyl, or substituted halocarbyl fragment;
L4 is the same group as L2, though, when L2 is defined as L1, L4 may be the same as L3 or L1;
R1 is a hydrocarbyl, substituted hydrocarbyl, halocarbyl, or substituted halocarbyl;
M1 is an element of group 1, 2, 12, 13 or 14 of the Periodic Table of the Elements, preferably Li, Na, K, Rb, Cs, Be, Mg, Ca, Sr, Ba, B, Si, Sn, Zn, Cd or Hg, more preferably B, Si, Sn, Zn, Cd or Hg, and most preferably B, Sn or Zn;
each X2, if present, is selected independently from the group consisting of halogen atoms, the hydroxyl group, alkoxy groups, aryloxy groups, mesylate, tosylate and triflate, preferably from the group consisting of halogen atoms, the hydroxyl group, alkoxy and aryloxy;
r is 1, 2 or 3, and
t is 0, 1 or 2, where r+t corresponds to the oxidation number of M1. - Conveniently, L1 is a substituted indenyl, a substituted heteroindenyl, a substituted fluorenyl, or a substituted heterofluorenyl ligand.
- Conveniently, L2 is a substituted or unsubstituted monocyclic or polycyclic ligand, preferably a substituted or unsubstitued cyclopentadienyl ligand, a substituted or unsubstituted heterocyclopentadienyl ligand, a substituted or unsubstituted indenyl ligand, a substituted or unsubstituted heteroindenyl ligand, a substituted or unsubstituted fluorenyl ligand, a substituted or unsubstituted heterofluorenyl ligand.
- Preferably, L1 comprises at least one chlorine, bromine, or triflate directly bonded to an sp2 carbon atom of the ring structure of the ligand, and most preferably L1 comprises at least one bromine or triflate directly bonded to an sp2 carbon atom of the ring structure of the ligand.
- In a second embodiment, the invention provides a process for preparing a chelating ligand of the formula (IIa), (IIb), or (IIc) from a chelating ligand of the formula (Ia), (Ib), or (Ic), respectively:
and a coupling component of the formula (III)
wherein
M1 is an element of group 1, 2, 12, 13 or 14 of the Periodic Table of the Elements, preferably Li, Na, K, Rb, Cs, Be, Mg, Ca, Sr, Ba, B, Si, Sn, Zn, Cd or Hg, more preferably B, Si, Sn, Zn, Cd or Hg, and most preferably B, Sn or Zn;
the or each X1 is a chlorine, bromine, iodine, triflate, or sulfonate group, preferably chlorine, bromine, or triflate, and more preferably bromine or triflate, and the or each X1 is directly bonded to an sp2 carbon atom of the ring structure of the ligand;
each X2, if present, is selected independently from the group consisting of halogen atoms, hydroxyl groups, alkoxy groups and aryloxy groups;
R1 is a hydrocarbyl, substituted hydrocarbyl, halocarbyl, or substituted halocarbyl;
R2, R3, R4, and R5 are, independently selected from hydrogen, hydrocarbyl, substituted hydrocarbyl, halocarbyl, substituted halocarbyl, silylcarbyl, germylcarbyl radicals and polar groups as defined above; provided that all R2 groups may be different and, optionally, adjacent R2, R3, R4, and R5 groups may also together form a cyclic aliphatic or aromatic ring system which may in turn be substituted and may contain heteroatoms; for example, the R3 and R4 groups together may form a cyclic aromatic or heteroaromatic ring, i.e. form fluorenyl or heterofluorenyl fragment in the formulas (Ia), (Ib), (Ic), (IIa), (IIb), and (IIc); and provided further that R2, R3, and R4 groups are attached to ring carbons; R5′ groups are attached to heteroatoms;
each Q, if present, is, independently, a Group 16 atom, a Group 15 atom, or boron, and preferably S, O, N, or P; when a Q is a Group 15 atom or boron, “q” is one, indicating the presence of one R5′ bonded to Q, and when a Q is a Group 16 atom, “q” is zero, indicating the absence of R5′; m, n, and p are independently zero or one, and m+n+p=1; when m or n or p is one, Q is present in the ring as a Group 16 or Group 15 atom or as boron; when m or n or p is zero, Q is absent and is replaced by a ring carbon atom having either a substituent R2 or a substituent X1;
each E, if present, is, independently, a Group 15 atom, preferably N or P; when E is present, it does not have any substituents; m, n, p, and s are independently zero or one, and m+n+p+s=1; when m or n or p or s is one, E is present in the ring as a Group 15 atom; when m or n or p or s is zero, E is absent and is replaced by a ring carbon atom having either a substituent R2 or a substituent X1;
B is a bridging group that contains a Group 13, 14, 15, or 16 element;
A is a substituted or unsubstituted monocyclic or polycyclic ligand, preferably a substituted or unsubstituted cyclopentadienyl, a substituted or unsubstituted heterocyclopentadienyl, a substituted or unsubstituted indenyl, a substituted or unsubstituted heteroindenyl, a substituted or unsubstituted fluorenyl, or a substituted or unsubstituted heterofluorenyl;
x represents the number of R2 substituents bonded to the aryl fused to the cyclopentadienyl in structures (Ia) and (IIa), the number of R2 substituents bonded to the 5-member heterocyclic fragment in the structures (Ib) and (IIb), or the number of R2 substituents bonded to the 6-member heterocyclic fragment in the structures (Ic) and (IIc);
x is 0, 1, 2, or 3 in structures (Ia) and (IIa);
x is 0 or 1 in structures (Ib) and (IIb);
x is 0, 1, or 2 in structures (Ic and IIc);
z represents the number of X1 substituents converted to R1 substituents and is 1, 2, 3, or 4 in structures (Ia) and (IIa); 1 or 2 in structures (Ib) and (IIb); and 1, 2, or 3 in structures (Ic) and (IIc);
x+z is 4 in structures (Ia) and (IIa);
x+z is 2 in structures (Ib) and (IIb);
x+z is 3 in structures (Ic) and (IIc);
r is 1, 2 or 3, and
t is 0, 1 or 2, where r+t corresponds to the oxidation number of M1. - In a third embodiment, the invention provides a process for preparing a chelating ligand of the formula (Va), (Vb), (Vc), (Vd), (Ve), (Vf), (Vg), (Vh), (Vi), (Vk), (Vm), (Vn), (Vo), (Vp), (Vq), (Vr), (Vs), (Vt), (Vu), (Vv), (Vw), (Vx), or (Vy) from a chelating ligand of the formula (IVa), (IVb), (IVc), (IVd), (IVe), (IVf), (IVg), (IVh), (IVi), (IVk), (UVm), (IVn), (IVo), (IVp), (IVq), (IVr), (IVs), (IVt), (IVu), (IVv), (IVw), (IVx), or (IVy), respectively, and a coupling component of the formula (III):
wherein:
M1 is an element of group 1, 2, 12, 13 or 14 of the Periodic Table of the Elements, preferably Li, Na, K, Rb, Cs, Be, Mg, Ca, Sr, Ba, B, Si, Sn, Zn, Cd or Hg, more preferably B, Si, Sn, Zn, Cd or Hg, and most preferably B, Sn or Zn;
X3, X4, X5, X6 are, independently, chlorine, bromine, iodine, triflate, or sulfonate groups, preferably chlorine, bromine, or triflate, and more preferably bromine or triflate; each X2, if present, is selected independently from the group consisting of halogen atoms, the hydroxyl groups, alkoxy groups and aryloxy groups;
R1 is a hydrocarbyl, substituted hydrocarbyl, halocarbyl, or substituted halocarbyl;
R3, R4, R5, R6, R7, R8, R9, R10, R11, R12 are, independently, hydrogen, hydrocarbyl, substituted hydrocarbyl, halocarbyl, substituted halocarbyl, silylcarbyl, germylcarbyl radical or polar group as defined above, where, optionally, adjacent R3, R4, R5, R6, R7, R8, R9, R10, R11, R12 groups may also together form a cyclic aliphatic or aromatic ring system which may in turn be substituted and may contain heteroatoms;
B is a bridging group that contains a Group 13, 14, 15, or 16 element;
r is 1, 2 or 3, and
t is 0, 1 or 2, where r+t corresponds to the oxidation number of M1. - In a fourth embodiment, the invention provides a process for preparing a chelating ligand of the formula (VIIa), (VIb), (VIc), (VIId), (VIIe), (VIIf), (VIIg), (VIIh), (VIIi), (VIIk), (VIIm), (VIIn), (VIIo), (VIIp), (VIIq), (VIIr), or (VIs) from a chelating ligand of the formula (VIa), (VIb), (VIc), (VId), (VIe), (VIf), (VIg), (VIh), (VIi), (VIk), (VIm), (VIn), (VIo), (VIp), (VIq), (VIr), or (VIs), respectively, and a coupling component of the formula (III):
wherein:
M1 is an element of group 1, 2, 12, 13 or 14 of the Periodic Table of the Elements, preferably Li, Na, K, Rb, Cs, Be, Mg, Ca, Sr, Ba, B, Si, Sn, Zn, Cd or Hg, more preferably B, Si, Sn, Zn, Cd or Hg, and most preferably B, Sn or Zn;
X3, X4, X5, X6 are, independently, chlorine, bromine, iodine, triflate, or sulfonate groups, preferably chlorine, bromine, or triflate, and more preferably, bromine or triflate;
each X2, if present, is selected independently from the group consisting of halogen atoms, the hydroxyl groups, alkoxy groups and aryloxy groups;
R1 is a hydrocarbyl, substituted hydrocarbyl, halocarbyl, or substituted halocarbyl;
R3, R4, R5, R6, R7, R8, R9, R10 are, independently, hydrogen, hydrocarbyl, substituted hydrocarbyl, halocarbyl, substituted halocarbyl, silylcarbyl, germylcarbyl radical or polar group as defined above, where, optionally, adjacent R3, R4, R5, R6, R7, R8, R9, and R10 groups may also together form a cyclic aliphatic or aromatic ring system which may in turn be substituted and may contain heteroatoms;
B is a bridging group that contains a Group 13, 14, 15, or 16 element;
r is 1, 2 or 3; and
t is 0, 1 or 2, where r+t corresponds to the oxidation number of M1. - In a fifth embodiment, the invention provides a process for preparing a chelating ligand of the formula (IId), (IId), or (IIf) from a chelating ligand of the formula (Id), (Ie), or (If), respectively, and a coupling component of the formula (III):
wherein:
M1 is an element of group 1, 2, 12, 13 or 14 of the Periodic Table of the Elements, preferably Li, Na, K, Rb, Cs, Be, Mg, Ca, Sr, Ba, B, Si, Sn, Zn, Cd or Hg, more preferably B, Si, Sn, Zn, Cd or Hg, and most preferably B, Sn or Zn;
each X1 is independently a chlorine, bromine, iodine, triflate, or sulfonate group, preferably chlorine, bromine, or triflate, and more preferably, bromine or triflate, and each X1 is directly bonded to an sp2 carbon atom of the ring structure of the ligand;
each X2, if present, is selected independently from the group consisting of halogen atoms, the hydroxyl groups, alkoxy groups and aryloxy groups;
R1 is a hydrocarbyl, substituted hydrocarbyl, halocarbyl, or substituted halocarbyl;
R2, R5′, and R6′ are, independently, hydrogen, hydrocarbyl, substituted hydrocarbyl, halocarbyl, substituted halocarbyl, silylcarbyl, germylcarbyl radical or polar group as defined above; provided that all R2 groups may be different and, optionally, adjacent R2, R5′, and R6′ groups may also together to form a cyclic aliphatic or aromatic ring system which may in turn be substituted and may contain heteroatoms; and provided further that R2 groups are attached to ring carbons; R5′ and R6′ groups are attached to heteroatoms;
B is a bridging group that contains a Group 13, 14, 15, or 16 element;
A is a substituted or unsubstituted monocyclic or polycyclic ligand, preferably a substituted or unsubstituted cyclopentadienyl, a substituted or unsubstituted heterocyclopentadienyl, a substituted or unsubstituted indenyl, a substituted or unsubstituted heteroindenyl, a substituted or unsubstituted fluorenyl, or a substituted or unsubstituted heterofluorenyl;
each Q, if present, is independently, a Group 16 atom, a Group 15 atom, or boron, and preferably S, O, N, or P; when a Q is a Group 15 atom or boron, “q” is one, indicating the presence of one R5 or R6, as the case may be, bonded to Q, and when a Q is a Group 16 atom, “q” is zero, indicating the absence of R5 or R6′, as the case may be; m, n, p, s, u, and v are independently zero or one, m+n+p=1, and s+u+v=1; when m or n or p or s or u or v is one, Q is present as a Group 16 or a Group 15 atom or as boron; when m or n or p or s or u or v is zero, Q is absent and is replaced by a ring carbon atom having either a substituent R2 or a substituent X1;
each E if present, is, independently, a Group 15 atom, preferably N or P; when E is present it does not have any substituents; m, n, p, s, u, v, w, and y are independently zero or one, m+n+p+s=1, and u+v+w+y=0 or 1; when m or n or p or s or u or v or w or y is present, E is present in the ring as a Group 15 atom; when m or n or p or s or u or v or w or y is zero, E is absent and is replaced by a ring carbon having either a substituent R2 or a substituent X1;
x1+x2 represents the total number of R2 substituents bonded to the fluorenyl ligand instructures (Id) and (IId) or the total number of R2 substituents bonded to the heterofluorenyl ligands in structures (Ie), (If), (IIe) and (IIf); x1+x2 is 0, 1, 2, 3, 4, 5, 6, or 7 in structures (Id) and (IId);
x1+x2 is 0, 1, 2, or 3 in structures (Ie) and (IIe);
x1+x2 is 0, 1, 2, 3, 4, or 5 in structures (If) and (IIf); z1+z2 represents the total number of X1 substituents converted to R1 substituents and bonded to the fluorenyl ligand in structures (Id) and (IId), or the number of X1 substituents converted to R1 substituents and bonded to the heterofluorenyl ligand in structures (Ie), (If), (IIe), and (IIf);
z1+z2 is 1, 2, 3, 4, 5, 6, 7, or 8 in structures (Id) and (IId);
z1+z2 is 1, 2, 3 or 4 in structures (Ie) and (IIe);
z1+z2 is 1, 2, 3, 4, 5, 6, or 7 in structures (If) and (IIf);
x1+x2+z1+z2 is 8 in structures (Id) and (IId);
x1+x2+z1+z2 is 4 in structures (Ie) and (IIe);
x1+x2+z1+z2 is 6 in structures (If) and (IIf) when u+v+w+y=1;
x1+x2+z1+z2 is 7 in structures (If) and (IIf) when u+v+w+y=0;
r is 1, 2 or 3, and
t is 0, 1 or 2, where r+t corresponds to the oxidation number of M1. - In a fifth embodiment, the invention provides a process for preparing a chelating ligand of the formula (IXa), (IXb), (IXc), (IXd), (IXe), (IXf), (IXg), (IXh), (IXi), or (IXk) from a chelating ligand of the formula (VIIIa), (VIIIb), (VIIIc), (VIIId), (VIIIe), (VIIIf), (VIIIg), (VIIIh), (VIIIi), or (VIIIk), respectively, and a coupling component of the formula (III):
wherein:
M1 is an element of group 1, 2, 12, 13 or 14 of the Periodic Table of the Elements, preferably Li, Na, K, Rb, Cs, Be, Mg, Ca, Sr, Ba, B, Si, Sn, Zn, Cd or Hg, more preferably B, Si, Sn, Zn, Cd or Hg, and most preferably B, Sn or Zn;
X3, X4 are, independently, a chlorine, bromine, iodine, triflate, or sulfonate group, preferably chlorine, bromine, or triflate, and more preferably, bromine or triflate;
each X2, if present, is selected independently from the group consisting of halogen atoms, the hydroxyl groups, alkoxy groups and aryloxy groups;
R1 is a hydrocarbyl, substituted hydrocarbyl, halocarbyl, or substituted halocarbyl;
R3, R4, R5, R6, R7, R8, R9, R10, R11, R12 are, independently, hydrogen, hydrocarbyl, substituted hydrocarbyl, halocarbyl, substituted halocarbyl, silylcarbyl, germylcarbyl radical or polar group as defined above, where, optionally, adjacent R3, R4, R5, R6, R7, R8, R9, R10, R11, R12 groups may also together form a cyclic aliphatic or aromatic ring system which may in turn be substituted and may contain heteroatoms;
B is a bridging group that contains a Group 13, 14, 15, or 16 element;
r is 1, 2 or 3, and
t is 0, 1 or 2, where r+t corresponds to the oxidation number of M1. - Conveniently, B in each of formulae given in all the embodiments of this invention is a bridging group containing boron or a Group 14, 15 or 16 element. Examples of suitable bridging groups include R′2C, R′2Si, R′2Ge, R′2CCR′2, R′2CCR′2CR′2, R′2CCR′2CR′2CR′2, R′C═CR′, R′C═CR′CR′2, R′2CCR′═CR′CR′2, R′C═CR′CR′═CR′, R′C═CR′CR′2CR′2, R′2CSiR′2, R′2SiSiR′2, R′2CSiR′2CR′2, R′2SiCR′2SiR′2, R′C═CR′SiR′2, R′2CGeR′2, R′2GeGeR′2, R′2CGeR′2CR′2, R′2GeCR′2GeR′2, R′2SiGeR′2, R′C═CR′GeR′2, R′B, R′2C—BR′, R′2C—BR′—CR′2, R′2C—O—CR′2, R′2CR′2C—CR′2CR′2, R′2C—O—CR′2CR′2, R′2C—OR′═CR′, R′2C—S—CR′2, R′2CR′2C—S—CR′2CR′2, R′2C—S—CR′2CR′2, R′2C—S—CR′═CR′, R′2C—Se—CR′2, R′2CR′2C—Se—CR′2CR′2, R′2C—Se—CR′2CR′2, R′2C—Se—CR′═CR′, R′2C—N═CR′, R′2C—NR′—CR′2, R′2CNR′—CR′2CR′2, R′2C—NR′—CR′═CR′, R′2CR′2C—NR′—CR′2CR′2, R′2C—P═CR′, and R′2C—PR′—CR12 where R′is hydrogen or a C1-C20 containing hydrocarbyl, substituted hydrocarbyl, halocarbyl, substituted halocarbyl, silylcarbyl or germylcarbyl substituent and optionally two or more adjacent R1 may join to form a substituted or unsubstituted, saturated, partially unsaturated or aromatic, cyclic or polycyclic substituent. Preferred examples for the bridging group Y include CH2, CH2CH2, CH(CH3)2, SiMe2, SiPh2, SiMePh, Si(CH2)3, and Si(CH2)4.
- Non-limiting examples of chelating ligands of the formula (I) include:
- bis(4-bromo-2-methylinden-1-yl)dimethylsilane,
- bis(4-bromoinden-1-yl)dimethylsilane,
- bis(4-bromoinden-2-yl)dimethylsilane,
- (4-bromoinden-1-yl)(4-bromoinden-2-yl)dimethylsilane,
- bis(4-chloro-2-methylinden-1-yl)dimethylsilane,
- bis(4-iodo-2-methylinden-1-yl)dimethylsilane,
- bis(4-bromo-2-methylinden-1-yl)diethylsilane,
- bis(4-bromo-2-methylinden-1-yl)methylphenylsilane,
- bis(4-bromo-2-methylinden-1-yl)diphenylsilane,
- bis(4-bromo-2-methylinden-1-yl)dimethylgermane,
- bis(4-bromo-2-methylinden-1-yl)phenylphosphine,
- bis(4-bromo-2-methylinden-1-yl)methylphosphine,
- bis(4-bromo-2-methylinden-1-yl)isopropylphosphine,
- 1,2-bis(4-bromo-2-methylinden-1-yl)-1′, 1″,2′,2″-tetramethyldisilane,
- 1,2-bis(4-bromo-2-methylinden-1-yl)ethane,
- cis-1,2-bis(4-bromo-2-methylinden-1-yl)ethylene,
- bis(4-bromo-2-methylinden-1-yl)methane,
- 2,2′-bis(4-bromo-2-methylinden-1-yl)propane,
- bis(4-bromo-2-methylinden-1-yl)diphenylmethane,
- bis(4,6-dibromo-2-methylinden-1-yl)dimethylsilane,
- bis(4-bromo-6-chloro-2-methylinden-1-yl)dimethylsilane,
- bis(4-bromo-2,6-dimethylinden-1-yl)dimethylsilane,
- bis(4-bromo-2-methyl-6-isopropylinden-1-yl)dimethylsilane,
- bis(4-bromo-2-methyl-6-fluoroinden-1-yl)dimethylsilane,
- bis(4-bromo-2-methyl-6-methoxyinden-1-yl)dimethylsilane,
- bis(4-bromo-2-methyl-6-dimethylaminoinden-1-yl)dimethylsilane,
- bis(4-bromo-2-methyl-6-diphenylphosphinoinden-1-yl)dimethylsilane,
- bis(4-bromo-2-methyl-6-methylsulfoinden-1-yl)dimethylsilane,
- bis(4-bromo-2-methyl-6-trimethylsilylinden-1-yl)dimethylsilane,
- bis(4-bromo-2-methyl-6-phenylinden-1-yl)dimethylsilane,
- bis(4-bromo-2-methyl-6-naphthylinden-1-yl)dimethylsilane,
- bis(4-bromo-2-methyl-6-N-indolylinden-1-yl)dimethylsilane,
- bis(4-bromo-2-methyl-6-trifluoromethylinden-1-yl)dimethylsilane,
- bis[4-bromo-2-methyl-6-(2-thienyl)inden-1-yl]dimethylsilane,
- bis[4-bromo-2-methyl-6-(4-pyridyl)inden-1-yl]dimethylsilane,
- bis(4-bromo-2-ethylinden-1-yl)dimethylsilane,
- bis(4-bromo-2-isopropylinden-1-yl)dimethylsilane,
- bis(4-bromo-2-phenylinden-1-yl)dimethylsilane,
- (4-bromo-2-methylinden-1-yl)(4-chloro-2-methylinden-1-yl)dimethylsilane,
- (4-bromo-2-methylinden-1-yl)(4-fluoro-2-methylinden-1-yl)dimethylsilane,
- (4-bromo-2-methylinden-1-yl)(4-iodo-2-methylinden-1-yl)dimethylsilane,
- (4-bromo-2-methylinden-1-yl)(2-methylinden-1-yl)dimethylsilane,
- (4-bromo-2-methylinden-1-yl)(2-isopropylinden-1-yl)dimethylsilane,
- (4-bromo-2-methylinden-1-yl)(inden-1-yl)dimethylsilane,
- (4-bromo-2-methylinden-1-yl)(inden-2-yl)dimethylsilane,
- (4-bromo-2-methylinden-1-yl)(2,4,6-trimethylinden-1-yl)dimethylsilane,
- (4-bromo-2-methylinden-1-yl)(4-phenyl-2-methylinden-1-yl)dimethylsilane,
- (4-bromo-2-methylinden-1-yl)(4-naphthyl-2-methylinden-1-yl)dimethylsilane,
- (4-bromo-2-methylinden-1-yl)[4-(2,5-dimethylphenyl)-2-methylinden-1-yl]dimethylsilane,
- (4-bromo-2-methylinden-1-yl)[4-(3,5-dimethylphenyl)-2-methylinden-1-yl]dimethylsilane,
- (4-bromo-2-methylinden-1-yl)[4-(3,5-diisopropylphenyl)-2-methylinden-1-yl]dimethylsilane,
- (4-bromo-2-methylinden-1-yl)[4-(3,5-di-tert-butylphenyl)-2-methylinden-1-yl]dimethylsilane,
- (4-bromo-2-methylinden-1-yl)[4-(2-thienyl)-2-methylinden-1-yl]dimethylsilane,
- (4-bromo-2-methylinden-1-yl)[4-(4-pyridyl)-2-methylinden-1-yl]dimethylsilane,
- (4-bromo-2-methylinden-1-yl)(4-tert-butyl-2-methylinden-1-yl)dimethylsilane,
- (4-bromo-2-methylinden-1-yl)(4-cyclohexyl-2-methylinden-1-yl)dimethylsilane,
- (4-bromo-2-methylinden-1-yl)(4-isopropyl-2-methylinden-1-yl)dimethylsilane,
- (4-bromo-2-methylinden-1-yl)(4-trimethysilyl-2-methylinden-1-yl)dimethylsilane,
- (4-bromo-2-methylinden-1-yl)(4-trimethylgermyl-2-methylinden-1-yl)dimethylsilane,
- (4-bromo-2-methylinden-1-yl)(4-methylthio-2-methylinden-1-yl)dimethylsilane,
- (4-bromo-2-methylinden-1-yl)(4-diphenylphosphino-2-methylinden-1-yl)dimethylsilane,
- (4-bromo-2-methylinden-1-yl)(4-trifluoromethyl-2-methylinden-1-yl)dimethylsilane,
- (4-bromo-2-methylinden-1-yl)(cyclopentadienyl)dimethylsilane,
- (4-bromo-2-methylinden-1-yl)(3-methylcyclopentadien-1-yl)dimethylsilane,
- (4-bromo-2-methylinden-1-yl)(3-tert-butylcyclopentadien-1-yl)dimethylsilane,
- (4-bromo-2-methylinden-1-yl)(3-trimethylsilylcyclopentadien-1-yl)dimethylsilane,
- (4-bromo-2-methylinden-1-yl)(3-phenylcyclopentadien-1-yl)dimethylsilane,
- (4-bromo-2-methylinden-1-yl)[3-(2-thienyl)cyclopentadien-1-yl]dimethylsilane,
- (4-bromo-2-methylinden-1-yl)(3-diphenylphosphinocyclopentadien-1-yl)dimethylsilane,
- (4-bromo-2-methylinden-1-yl)(2,3,4,5-tetramethylcyclopentadien-1-yl)dimethylsilane,
- (4-bromo-2-methylinden-1-yl)(fluoren-9-yl)dimethylsilane,
- (4-bromo-2-methylinden-1-yl)(3,6-dimethylfluoren-9-yl)dimethylsilane,
- (4-bromo-2-methylinden-1-yl)(3,6-di-tert-butylfluoren-9-yl)dimethylsilane,
- (4-bromo-2-methylinden-1-yl)(2,7-dibromofluoren-9-yl)dimethylsilane,
- (2-methylinden-1-yl)(2,7-dibromofluoren-9-yl)dimethylsilane,
- (2-methylinden-1-yl)(2,7-dichlorofluoren-9-yl)dimethylsilane,
- (2-methylinden-1-yl)(2,7-diiodofluoren-9-yl)dimethylsilane,
- (2-methyl-4-phenylinden-1-yl)(2,7-dibromofluoren-9-yl)dimethylsilane,
- (2,4-dimethylinden-1-yl)(2,7-dibromofluoren-9-yl)dimethylsilane,
- (2-methyl-4-trimethylsilylinden-1-yl)(2,7-dibromofluoren-9-yl)dimethylsilane,
- (2-methyl-4-tert-butylinden-1-yl)(2,7-dibromofluoren-9-yl)dimethylsilane,
- (2-methyl-4-methoxyinden-1-yl)(2,7-dibromofluoren-9-yl)dimethylsilane,
- (2-methyl-4-dimethylaminoinden-1-yl)(2,7-dibromofluoren-9-yl)dimethylsilane,
- (2-methyl-4-trifluoromethylinden-1-yl)(2,7-dibromofluoren-9-yl)dimethylsilane,
- (cyclopentadienyl)(2,7-dibromofluoren-9-yl)dimethylsilane,
- (3-methylcyclopentadien-1-yl)(2,7-dibromofluoren-9-yl)dimethylsilane,
- (3-tert-butylcyclopentadien-1-yl)(2,7-dibromofluoren-9-yl)dimethylsilane,
- (3-phenylcyclopentadien-1-yl)(2,7-dibromofluoren-9-yl)dimethylsilane,
- (3-trimethylsilylcyclopentadien-1-yl)(2,7-dibromofluoren-9-yl)dimethylsilane,
- (3,4-dimethylcyclopentadien-1-yl)(2,7-dibromofluoren-9-yl)dimethylsilane,
- [3-(2-thienyl)cyclopentadien-1-yl](2,7-dibromofluoren-9-yl)dimethylsilane,
- (fluoren-9-yl)(2,7-dibromofluoren-9-yl)dimethylsilane,
- (3,6-dimethylfluoren-9-yl)(2,7-dibromofluoren-9-yl)dimethylsilane,
- (3,6-ditertbutylfluoren-9-yl)(2,7-dibromofluoren-9-yl)dimethylsilane,
- (3,6-diphenylfluoren-9-yl)(2,7-dibromofluoren-9-yl)dimethylsilane,
- bis(4-bromo-2-methyl-5,6,7,8-tetrahydrocyclopenta[b]naphth-1-yl)dimethylsilane,
- bis(5-bromo-2-methyl-6,7,8,9-tetrahydrocyclopenta[a]naphth-3-yl)dimethylsilane,
- bis(4-bromo-2-methylcyclopenta[b]naphth-1-yl)dimethylsilane,
- bis(7-bromo-2,4-dimethylcyclopenta[b]naphth-1-yl)dimethylsilane,
- bis(8-bromo-6-methylindeno[5,6-d][1,3]dioxol-5-yl)dimethylsilane,
- bis(4-bromo-2,3,6-trimethylindeno[5,6-b]thien-7-yl)dimethylsilane,
- bis(2-bromo-4,6-dimethylindeno[5,6-b]thien-7-yl)dimethylsilane,
- bis(4-bromo-1,2,3,6-tetramethylcyclopenta[f]indol-7-yl)dimethylsilane,
- bis(4-bromo-1-phenyl-2,3,6-trimethylcyclopenta[f]indol-7-yl)dimethylsilane,
- bis(5-bromo-7-methylcyclopenta[g]quinol-8-yl)dimethylsilane,
- bis(2-bromo-5,7-dimethylcyclopenta[g]quinol-8-yl)dimethylsilane,
- (cyclopentadienyl)(4-bromo-2-methyl-5,6,7,8-tetrahydrocyclopenta[b]naphth-1-yl)dimethylsilane,
- (cyclopentadienyl)(5-bromo-2-methyl-6,7,8,9-tetrahydrocyclopenta[a]naphth-3-yl)dimethylsilane,
- (cyclopentadienyl)(4-bromo-2-methylcyclopenta[b]naphth-1-yl)dimethylsilane,
- (cyclopentadienyl)(7-bromo-2,4-dimethylcyclopenta[b]naphth-1-yl)dimethylsilane,
- (cyclopentadienyl)(8-bromo-6-methylindeno[5,6-d][1,3]dioxol-5-yl)dimethylsilane,
- (cyclopentadienyl)(4-bromo-2,3,6-trimethylindeno[5,6-b]thien-7-yl)dimethylsilane,
- (cyclopentadienyl)(2-bromo-4,6-dimethylindeno[5,6-b]thien-7-yl)dimethylsilane,
- (cyclopentadienyl)(4-bromo-1,2,3,6-tetramethylcyclopenta[/]indol-7-yl)dimethylsilane,
- (cyclopentadienyl)(4-bromo-1-phenyl-2,3,6-trimethylcyclopenta[f]indol-7-yl)dimethylsilane,
- (cyclopentadienyl)(5-bromo-7-methylcyclopenta[g]quinol-8-yl)dimethylsilane,
- (cyclopentadienyl)(2-bromo-5,7-dimethylcyclopenta[g]quinol-8-yl)dimethylsilane,
- (inden-1-yl)(4-bromo-2-methyl-5,6,7,8-tetrahydrocyclopenta[b]naphth-1-yl)dimethylsilane,
- (inden-1-yl)(5-bromo-2-methyl-6,7,8,9-tetrahydrocyclopenta[a]naphth-3-yl)dimethylsilane,
- (inden-1-yl)(4-bromo-2-methylcyclopenta[b]naphth-1-yl)dimethylsilane,
- (inden-1-yl)(7-bromo-2,4-dimethylcyclopenta[b]naphth-1-yl)dimethylsilane,
- (inden-1-yl)(8-bromo-6-methylindeno[5,6-d][1,3]dioxol-5-yl)dimethylsilane,
- (inden-1-yl)(4-bromo-2,3,6-trimethylindeno[5,6-b]thien-7-yl)dimethylsilane,
- (inden-1-yl)(2-bromo-4,6-dimethylindeno[5,6-b]thien-7-yl)dimethylsilane,
- (inden-1-yl)(4-bromo-1,2,3,6-tetramethylcyclopenta[f]indol-7-yl)dimethylsilane,
- (inden-1-yl)(4-bromo-1-phenyl-2,3,6-trimethylcyclopenta[f]indol-7-yl)dimethylsilane,
- (inden-1-yl)(5-bromo-7-methylcyclopenta[g]quinol-8-yl)dimethylsilane,
- (inden-1-yl)(2-bromo-5,7-dimethylcyclopenta[g]quinol-8-yl)dimethylsilane,
- (inden-2-yl)(4-bromo-2-methyl-5,6,7,8-tetrahydrocyclopenta[b]naphth-1-yl)dimethylsilane,
- (inden-2-yl)(5-bromo-2-methyl-6,7,8,9-tetrahydrocyclopenta[a]naphth-3-yl)dimethylsilane,
- (inden-2-yl)(4-bromo-2-methylcyclopenta[b]naphth-1-yl)dimethylsilane,
- (inden-2-yl)(7-bromo-2,4-dimethylcyclopenta[b]naphth-1-yl)dimethylsilane,
- (inden-2-yl)(8-bromo-6-methylindeno[5,6-d][1,3]dioxol-5-yl)dimethylsilane,
- (inden-2-yl)(4-bromo-2,3,6-trimethylindeno[5,6-b]thien-7-yl)dimethylsilane,
- (inden-2-yl)(2-bromo-4,6-dimethylindeno[5,6-b]thien-7-yl)dimethylsilane,
- (inden-2-yl)(4-bromo-1,2,3,6-tetramethylcyclopenta[/]indol-7-yl)dimethylsilane,
- (inden-2-yl)(4-bromo-1-phenyl-2,3,6-trimethylcyclopenta[/]indol-7-yl)dimethylsilane,
- (inden-2-yl)(5-bromo-7-methylcyclopenta[g]quinol-8-yl)dimethylsilane,
- (inden-2-yl)(2-bromo-5,7-dimethylcyclopenta[g]quinol-8-yl)dimethylsilane,
- (4-bromo-2-methylinden-1-yl)(4-bromo-2-methyl-5,6,7,8-tetrahydrocyclopenta[b]naphth-1-yl)dimethylsilane,
- (4-bromo-2-methylinden-1-yl)(5-bromo-2-methyl-6,7,8,9-tetrahydrocyclopenta[a]naphth-3-yl)dimethylsilane,
- (4-bromo-2-methylinden-1-yl)(4-bromo-2-methylcyclopenta[b]naphth-1-yl)dimethylsilane,
- (4-bromo-2-methylinden-1-yl)(7-bromo-2,4-dimethylcyclopenta[b]naphth-1-yl)dimethylsilane,
- (4-bromo-2-methylinden-1-yl)(8-bromo-6-methylindeno[5,6-d][1,3]dioxol-5-yl)dimethylsilane,
- (4-bromo-2-methylinden-1-yl)(4-bromo-2,3,6-trimethylindeno[5,6-b]thien-7-yl)dimethylsilane,
- (4-bromo-2-methylinden-1-yl)(2-bromo-4,6-dimethylindeno[5,6-b]thien-7-yl)dimethylsilane,
- (4-bromo-2-methylinden-1-yl)(4-bromo-1,2,3,6-tetramethylcyclopenta[/]indol-7-yl)dimethylsilane,
- (4-bromo-2-methylinden-1-yl)(4-bromo-1-phenyl-2,3,6-trimethylcyclopenta[f]indol-7-yl)dimethylsilane,
- (4-bromo-2-methylinden-1-yl)(5-bromo-7-methylcyclopenta[g]quinol-8-yl)dimethylsilane,
- (4-bromo-2-methylinden-1-yl)(2-bromo-5,7-dimethylcyclopenta[g]quinol-8-yl)dimethylsilane,
- (fluoren-9-yl)(4-bromo-2-methyl-5,6,7,8-tetrahydrocyclopenta[b]naphth-1-yl)dimethylsilane,
- (fluoren-9-yl)(5-bromo-2-methyl-6,7,8,9-tetrahydrocyclopenta[a]naphth-3-yl)dimethylsilane,
- (fluoren-9-yl)(4-bromo-2-methylcyclopenta[b]naphth-1-yl)dimethylsilane,
- (fluoren-9-yl)(7-bromo-2,4-dimethylcyclopenta[b]naphth-1-yl)dimethylsilane,
- (fluoren-9-yl)(8-bromo-6-methylindeno[5,6-d][1,3]dioxol-5-yl)dimethylsilane,
- (fluoren-9-yl)(4-bromo-2,3,6-trimethylindeno[5,6-b]thien-7-yl)dimethylsilane,
- (fluoren-9-yl)(2-bromo-4,6-dimethylindeno[5,6-b]thien-7-yl)dimethylsilane,
- (fluoren-9-yl)(4-bromo-1,2,3,6-tetramethylcyclopenta[f]indol-7-yl)dimethylsilane,
- (fluoren-9-yl)(4-bromo-1-phenyl-2,3,6-trimethylcyclopenta[/]indol-7-yl)dimethylsilane,
- (fluoren-9-yl)(5-bromo-7-methylcyclopenta[g]quinol-8-yl)dimethylsilane,
- (fluoren-9-yl)(2-bromo-5,7-dimethylcyclopenta[g]quinol-8-yl)dimethylsilane,
- 2,2′-bis(4-bromo-3-dimethylamino-1,3-benzothiaborollide)dimethylsilane,
- bis(4-bromo-3a,7a-azaborollide)dimethylsilane,
- 3,3′-bis(7-bromo-2-dimethylamino-1,2-benzothiaborollide)dimethylsilane,
- 5,5′-bis(3-bromo-2-dimethylamino-1,2-thiaborollide)dimethylsilane,
- 2,2′-(cyclopentadienyl)(4-bromo-3-dimethylamino-1,3-benzothiaborollide)dimethylsilane,
- (cyclopentadienyl)(4-bromo-3a,7a-azaborinden-1-yl)dimethylsilane,
- 1,3′-(cyclopentadienyl)(7-bromo-2-dimethylamino-1,2-benzothiaborollide)dimethylsilane,
- 1,5′-(cyclopentadienyl)(3-bromo-2-dimethylamino-1,2-thiaborollide)dimethylsilane,
- 1,2′-(indenyl)(4-bromo-3-dimethylamino-1,3-benzothiaborollide)dimethylsilane,
- (inden-1-yl)(4-bromo-3a,7a-azaborinden-1-yl)dimethylsilane,
- 1,3′-(indenyl)(7-bromo-2-dimethylamino-1,2-benzothiaborollide)dimethylsilane,
- 1,5′-(indenyl)(3-bromo-2-dimethylamino-1,2-thiaborollide)dimethylsilane,
- 2,2′-(indenyl)(4-bromo-3-dimethylamino-1,3-benzothiaborollide)dimethylsilane,
- (inden-2-yl)(4-bromo-3a,7a-azaborinden-1-yl)dimethylsilane,
- 2,3′-(indenyl)(7-bromo-2-dimethylamino-1,2-benzothiaborollide)dimethylsilane,
- 2,5′-(indenyl)(3-bromo-2-dimethylamino-1,2-thiaborollide)dimethylsilane,
- 9,2′-(fluorenyl)(4-bromo-3-dimethylamino-1,3-benzothiaborollide)dimethylsilane,
- (fluoren-9-yl)(4-bromo-3a,7a-azaborinden-1-yl)dimethylsilane,
- 9,3′-(fluorenyl)(7-bromo-2-dimethylamino-1,2-benzothiaborollide)dimethylsilane,
- 9,5′-(fluorenyl)(3-bromo-2-dimethylamino-1,2-thiaborollide)dimethylsilane,
- bis(4-bromoinden-1-yl)methane,
- bis(4-bromoinden-2-yl)methane,
- (4-bromoinden-1-yl)(4-bromoinden-2-yl)methane,
- bis(4-chloro-2-methylinden-1-yl)methane,
- bis(4-iodo-2-methylinden-1-yl)methane,
- bis(4,6-dibromo-2-methylinden-1-yl)methane,
- bis(4-bromo-6-chloro-2-methylinden-1-yl)methane,
- bis(4-bromo-2,6-dimethylinden-1-yl)methane,
- bis(4-bromo-2-methyl-6-isopropylinden-1-yl)methane,
- bis(4-bromo-2-methyl-6-fluoroinden-1-yl)methane,
- bis(4-bromo-2-methyl-6-methoxyinden-1-yl)methane,
- bis(4-bromo-2-methyl-6-dimethylaminoinden-1-yl)methane,
- bis(4-bromo-2-methyl-6-diphenylphosphinoinden-1-yl)methane,
- bis(4-bromo-2-methyl-6-methylsulfoinden-1-yl)methane,
- bis(4-bromo-2-methyl-6-trimethylsilylinden-1-yl)methane,
- bis(4-bromo-2-methyl-6-phenylinden-1-yl)methane,
- bis(4-bromo-2-methyl-6-naphthylinden-1-yl)methane,
- bis(4-bromo-2-methyl-6-N-indolylinden-1-yl)methane,
- bis(4-bromo-2-methyl-6-trifluoromethylinden-1-yl)methane,
- bis[4-bromo-2-methyl-6-(2-thienyl)inden-1-yl]methane,
- bis[4-bromo-2-methyl-6-(4-pyridyl)inden-1-yl]methane,
- bis(4-bromo-2-ethylinden-1-yl)methane,
- bis(4-bromo-2-isopropylinden-1-yl)methane,
- bis(4-bromo-2-phenylinden-1-yl)methane,
- (4-bromo-2-methylinden-1-yl)(4-chloro-2-methylinden-1-yl)methane,
- (4-bromo-2-methylinden-1-yl)(4-fluoro-2-methylinden-1-yl)methane,
- (4-bromo-2-methylinden-1-yl)(4-iodo-2-methylinden-1-yl)methane,
- (4-bromo-2-methylinden-1-yl)(2-methylinden-1-yl)methane,
- (4-bromo-2-methylinden-1-yl)(2-isopropylinden-1-yl)methane,
- (4-bromo-2-methylinden-1-yl)(inden-1-yl)methane,
- (4-bromo-2-methylinden-1-yl)(inden-2-yl)methane,
- (4-bromo-2-methylinden-1-yl)(2,4,6-trimethylinden-1-yl)methane,
- (4-bromo-2-methylinden-1-yl)(4-phenyl-2-methylinden-1-yl)methane,
- (4-bromo-2-methylinden-1-yl)(4-naphthyl-2-methylinden-1-yl)methane,
- (4-bromo-2-methylinden-1-yl)[4-(2,5-dimethylphenyl)-2-methylinden-1-yl]methane,
- (4-bromo-2-methylinden-1-yl)[4-(3,5-dimethylphenyl)-2-methylinden-1-yl]methane,
- (4-bromo-2-methylinden-1-yl)[4-(3,5-diisopropylphenyl)-2-methylinden-1-yl]methane,
- (4-bromo-2-methylinden-1-yl)[4-(3,5-di-tert-butylphenyl)-2-methylinden-1-yl]methane,
- (4-bromo-2-methylinden-1-yl)[4-(2-thienyl)-2-methylinden-1-yl]methane,
- (4-bromo-2-methylinden-1-yl)[4-(4-pyridyl)-2-methylinden-1-yl]methane,
- (4-bromo-2-methylinden-1-yl)(4-tert-butyl-2-methylinden-1-yl)methane,
- (4-bromo-2-methylinden-1-yl)(4-cyclohexyl-2-methylinden-1-yl)methane,
- (4-bromo-2-methylinden-1-yl)(4-isopropyl-2-methylinden-1-yl)methane,
- (4-bromo-2-methylinden-1-yl)(4-trimethysilyl-2-methylinden-1-yl)methane,
- (4-bromo-2-methylinden-1-yl)(4-trimethylgermyl-2-methylinden-1-yl)methane,
- (4-bromo-2-methylinden-1-yl)(4-methylthio-2-methylinden-1-yl)methane,
- (4-bromo-2-methylinden-1-yl)(4-diphenylphosphino-2-methylinden-1-yl)methane,
- (4-bromo-2-methylinden-1-yl)(4-trifluoromethyl-2-methylinden-1-yl)methane,
- (4-bromo-2-methylinden-1-yl)(cyclopentadienyl)methane,
- (4-bromo-2-methylinden-1-yl)(3-methylcyclopentadien-1-yl)methane,
- (4-bromo-2-methylinden-1-yl)(3-tert-butylcyclopentadien-1-yl)methane,
- (4-bromo-2-methylinden-1-yl)(3-trimethylsilylcyclopentadien-1-yl)methane,
- (4-bromo-2-methylinden-1-yl)(3-phenylcyclopentadien-1-yl)methane,
- (4-bromo-2-methylinden-1-yl)[3-(2-thienyl)cyclopentadien-1-yl]methane,
- (4-bromo-2-methylinden-1-yl)(3-diphenylphosphinocyclopentadien-1-yl)methane,
- (4-bromo-2-methylinden-1-yl)(2,3,4,5-tetramethylcyclopentadien-1-yl)methane,
- (4-bromo-2-methylinden-1-yl)(fluoren-9-yl)methane,
- (4-bromo-2-methylinden-1-yl)(3,6-dimethylfluoren-9-yl)methane,
- (4-bromo-2-methylinden-1-yl)(3,6-di-tert-butylfluoren-9-yl)methane,
- (4-bromo-2-methylinden-1-yl)(2,7-dibromofluoren-9-yl)methane,
- (2-methylinden-1-yl)(2,7-dibromofluoren-9-yl)methane,
- (2-methylinden-1-yl)(2,7-dichlorofluoren-9-yl)methane,
- (2-methylinden-1-yl)(2,7-diiodofluoren-9-yl)methane,
- (2-methyl-4-phenylinden-1-yl)(2,7-dibromofluoren-9-yl)methane,
- (2,4-dimethylinden-1-yl)(2,7-dibromofluoren-9-yl)methane,
- (2-methyl-4-trimethylsilylinden-1-yl)(2,7-dibromofluoren-9-yl)methane,
- (2-methyl-4-tert-butylinden-1-yl)(2,7-dibromofluoren-9-yl)methane,
- (2-methyl-4-methoxyinden-1-yl)(2,7-dibromofluoren-9-yl)methane,
- (2-methyl-4-dimethylaminoinden-1-yl)(2,7-dibromofluoren-9-yl)methane,
- (2-methyl-4-trifluoromethylinden-1-yl)(2,7-dibromofluoren-9-yl)methane,
- (cyclopentadienyl)(2,7-dibromofluoren-9-yl)methane,
- (3-methylcyclopentadien-1-yl)(2,7-dibromofluoren-9-yl)methane,
- (3-tert-butylcyclopentadien-1-yl)(2,7-dibromofluoren-9-yl)methane,
- (3-phenylcyclopentadien-1-yl)(2,7-dibromofluoren-9-yl)methane,
- (3-trimethylsilylcyclopentadien-1-yl)(2,7-dibromofluoren-9-yl)methane,
- (3,4-dimethylcyclopentadien-1-yl)(2,7-dibromofluoren-9-yl)methane,
- [3-(2-thienyl)cyclopentadien-1-yl](2,7-dibromofluoren-9-yl)methane,
- (fluoren-9-yl)(2,7-dibromofluoren-9-yl)methane,
- (3,6-dimethylfluoren-9-yl)(2,7-dibromofluoren-9-yl)methane,
- (3,6-ditertbutylfluoren-9-yl)(2,7-dibromofluoren-9-yl)methane,
- (3,6-diphenylfluoren-9-yl)(2,7-dibromofluoren-9-yl)methane,
- bis(4-bromo-2-methyl-5,6,7,8-tetrahydrocyclopenta[b]naphth-1-yl)methane,
- bis(5-bromo-2-methyl-6,7,8,9-tetrahydrocyclopenta[a]naphth-3-yl)methane,
- bis(4-bromo-2-methylcyclopenta[b]naphth-1-yl)methane,
- bis(7-bromo-2,4-dimethylcyclopenta[b]naphth-1-yl)methane,
- bis(8-bromo-6-methylindeno[5,6-d][1,3]dioxol-5-yl)methane,
- bis(4-bromo-2,3,6-trimethylindeno[5,6-b]thien-7-yl)methane,
- bis(2-bromo-4,6-dimethylindeno[5,6-b]thien-7-yl)methane,
- bis(4-bromo-1,2,3,6-tetramethylcyclopenta[f]indol-7-yl)methane,
- bis(4-bromo-1-phenyl-2,3,6-trimethylcyclopenta[f]indol-7-yl)methane,
- bis(5-bromo-7-methylcyclopenta[g]quinol-8-yl)methane,
- bis(2-bromo-5,7-dimethylcyclopenta[g]quinol-8-yl)methane,
- (cyclopentadienyl)(4-bromo-2-methyl-5,6,7,8-tetrahydrocyclopenta[b]naphth-1-yl)methane,
- (cyclopentadienyl)(5-bromo-2-methyl-6,7,8,9-tetrahydrocyclopenta[a]naphth-3-yl)methane,
- (cyclopentadienyl)(4-bromo-2-methylcyclopenta[b]naphth-1-yl)methane,
- (cyclopentadienyl)(7-bromo-2,4-dimethylcyclopenta[b]naphth-1-yl)methane,
- (cyclopentadienyl)(8-bromo-6-methylindeno[5,6-d][1,3]dioxol-5-yl)methane,
- (cyclopentadienyl)(4-bromo-2,3,6-trimethylindeno[5,6-b]thien-7-yl)methane,
- (cyclopentadienyl)(2-bromo-4,6-dimethylindeno[5,6-b]thien-7-yl)methane,
- (cyclopentadienyl)(4-bromo-1,2,3,6-tetramethylcyclopenta[f]indol-7-yl)methane,
- (cyclopentadienyl)(4-bromo-1-phenyl-2,3,6-trimethylcyclopenta[/]indol-7-yl)methane,
- (cyclopentadienyl)(5-bromo-7-methylcyclopenta[g]quinol-8-yl)methane,
- (cyclopentadienyl)(2-bromo-5,7-dimethylcyclopenta[g]quinol-8-yl)methane,
- (inden-1-yl)(4-bromo-2-methyl-5,6,7,8-tetrahydrocyclopenta[b]naphth-1-yl)methane,
- (inden-1-yl)(5-bromo-2-methyl-6,7,8,9-tetrahydrocyclopenta[a]naphth-3-yl)methane,
- (inden-1-yl)(4-bromo-2-methylcyclopenta[b]naphth-1-yl)methane,
- (inden-1-yl)(7-bromo-2,4-dimethylcyclopenta[b]naphth-1-yl)methane,
- (inden-1-yl)(8-bromo-6-methylindeno[5,6-d][1,3]dioxol-5-yl)methane,
- (inden-1-yl)(4-bromo-2,3,6-trimethylindeno[5,6-b]thien-7-yl)methane,
- (inden-1-yl)(2-bromo-4,6-dimethylindeno[5,6-b]thien-7-yl)methane,
- (inden-1-yl)(4-bromo-1,2,3,6-tetramethylcyclopenta[f]indol-7-yl)methane,
- (inden-1-yl)(4-bromo-1-phenyl-2,3,6-trimethylcyclopenta[/]indol-7-yl)methane,
- (inden-1-yl)(5-bromo-7-methylcyclopenta[g]quinol-8-yl)methane,
- (inden-1-yl)(2-bromo-5,7-dimethylcyclopenta[g]quinol-8-yl)methane,
- (inden-2-yl)(4-bromo-2-methyl-5,6,7,8-tetrahydrocyclopenta[b]naphth-1-yl)methane,
- (inden-2-yl)(5-bromo-2-methyl-6,7,8,9-tetrahydrocyclopenta[a]naphth-3-yl)methane,
- (inden-2-yl)(4-bromo-2-methylcyclopenta[b]naphth-1-yl)methane,
- (inden-2-yl)(7-bromo-2,4-dimethylcyclopenta[b]naphth-1-yl)methane,
- (inden-2-yl)(8-bromo-6-methylindeno[5,6-d][1,3]dioxol-5-yl)methane,
- (inden-2-yl)(4-bromo-2,3,6-trimethylindeno[5,6-b]thien-7-yl)methane,
- (inden-2-yl)(2-bromo-4,6-dimethylindeno[5,6-b]thien-7-yl)methane,
- (inden-2-yl)(4-bromo-1,2,3,6-tetramethylcyclopenta[f]indol-7-yl)methane,
- (inden-2-yl)(4-bromo-1-phenyl-2,3,6-trimethylcyclopenta[f]indol-7-yl)methane,
- (inden-2-yl)(4-bromocyclopenta[b]pyrid-7-yl)methane,
- (inden-2-yl)(5-bromo-7-methylcyclopenta[g]quinol-8-yl)methane,
- (inden-2-yl)(2-bromo-5,7-dimethylcyclopenta[g]quinol-8-yl)methane,
- (4-bromo-2-methylinden-1-yl)(4-bromo-2-methyl-5,6,7,8-tetrahydrocyclopenta[b]naphth-1-yl)methane,
- (4-bromo-2-methylinden-1-yl)(5-bromo-2-methyl-6,7,8,9-tetrahydrocyclopenta[a]naphth-3-yl)methane,
- (4-bromo-2-methylinden-1-yl)(4-bromo-2-methylcyclopenta[b]naphth-1-yl)methane,
- (4-bromo-2-methylinden-1-yl)(7-bromo-2,4-dimethylcyclopenta[b]naphth-1-yl)methane,
- (4-bromo-2-methylinden-1-yl)(8-bromo-6-methylindeno[5,6-d][1,3]dioxol-5-yl)methane,
- (4-bromo-2-methylinden-1-yl)(4-bromo-2,3,6-trimethylindeno[5,6-b]thien-7-yl)methane,
- (4-bromo-2-methylinden-1-yl)(2-bromo-4,6-dimethylindeno[5,6-b]thien-7-yl)methane,
- (4-bromo-2-methylinden-1-yl)(4-bromo-1,2,3,6-tetramethylcyclopenta[f]indol-7-yl)methane,
- (4-bromo-2-methylinden-1-yl)(4-bromo-1-phenyl-2,3,6-trimethylcyclopenta[/]indol-7-yl)methane,
- (4-bromo-2-methylinden-1-yl)(5-bromo-7-methylcyclopenta[g]quinol-8-yl)methane,
- (4-bromo-2-methylinden-1-yl)(2-bromo-5,7-dimethylcyclopenta[g]quinol-8-yl)methane,
- (fluoren-9-yl)(4-bromo-2-methyl-5,6,7,8-tetrahydrocyclopenta[b]naphth-1-yl)methane,
- (fluoren-9-yl)(5-bromo-2-methyl-6,7,8,9-tetrahydrocyclopenta[a]naphth-3-yl)methane,
- (fluoren-9-yl)(4-bromo-2-methylcyclopenta[b]naphth-1-yl)methane,
- (fluoren-9-yl)(7-bromo-2,4-dimethylcyclopenta[b]naphth-1-yl)methane,
- (fluoren-9-yl)(8-bromo-6-methylindeno[5,6-d][1,3]dioxol-5-yl)methane,
- (fluoren-9-yl)(4-bromo-2,3,6-trimethylindeno[5,6-b]thien-7-yl)methane,
- (fluoren-9-yl)(2-bromo-4,6-dimethylindeno[5,6-b]thien-7-yl)methane,
- (fluoren-9-yl)(4-bromo-1,2,3,6-tetramethylcyclopenta[f]indol-7-yl)methane,
- (fluoren-9-yl)(4-bromo-1-phenyl-2,3,6-trimethylcyclopenta[f]indol-7-yl)methane,
- (fluoren-9-yl)(5-bromo-7-methylcyclopenta[g]quinol-8-yl)methane,
- (fluoren-9-yl)(4-bromocyclopenta[b]pyrid-7-yl)methane,
- (fluoren-9-yl)(2-bromo-5,7-dimethylcyclopenta[g]quinol-8-yl)methane,
- 2,2′-bis(4-bromo-3-dimethylamino-1,3-benzothiaborollide)methane,
- bis(4-bromo-3a,7a-azaborinden-1-yl)methane,
- 3,3′-bis(7-bromo-2-dimethylamino-1,2-benzothiaborollide)methane,
- 5,5′-bis(3-bromo-2-dimethylamino-1,2-thiaborollide)methane,
- 1,2′-(cyclopentadienyl)(4-bromo-3-dimethylamino-1,3-benzothiaborollide)methane,
- (cyclopentadienyl)(4-bromo-3a,7a-azaborinden-1-yl)methane,
- 1,3′-(cyclopentadienyl)(7-bromo-2-dimethylamino-1,2-benzothiaborollide)methane,
- 1,5′-(cyclopentadienyl)(3-bromo-2-dimethylamino-1,2-thiaborollide)methane,
- 1,2′-(inden-1-yl)(4-bromo-3-dimethylamino-1,3-benzothiaborollide)methane,
- (inden-1-yl)(4-bromo-3a,7a-azaborinden-1-yl)methane,
- 1,3′-(inden-1-yl)(7-bromo-2-dimethylamino-1,2-benzothiaborollide)methane,
- 1,5′-(inden-1-yl)(3-bromo-2-dimethylamino-1,2-thiaborollide)methane,
- 2,2′-(inden-2-yl)(4-bromo-3-dimethylamino-1,3-benzothiaborollide)methane,
- (inden-2-yl)(4-bromo-3a,7a-azaborinden-1-yl)methane,
- 2,3′-(inden-2-yl)(7-bromo-2-dimethylamino-1,2-benzothiaborollide)methane,
- 2,5′-(inden-2-yl)(3-bromo-2-dimethylamino-1,2-thiaborollide)methane,
- 9,2′-(fluoren-9-yl)(4-bromo-3-dimethylamino-1,3-benzothiaborollide)methane,
- (fluoren-9-yl)(4-bromo-3a,7a-azaborinden-1-yl)methane,
- 9,3′-(fluoren-9-yl)(7-bromo-2-dimethylamino-1,2-benzothiaborolidei)methane,
- 9,5′-(fluoren-9-yl)(3-bromo-2-dimethylamino-1,2-thiaborollide)methane,
- 2,2-bis(4-bromoinden-1-yl)propane,
- 2,2-bis(4-bromoinden-2-yl)propane,
- 2-(4-bromoinden-1-yl)-2-(4-bromoinden-2-yl)propane,
- 2,2-bis(4-chloro-2-methylinden-1-yl)propane,
- 2,2-bis(4-iodo-2-methylinden-1-yl)propane,
- 2,2-bis(4,6-dibromo-2-methylinden-1-yl)propane,
- 2,2-bis(4-bromo-6-chloro-2-methylinden-1-yl)propane,
- 2,2-bis(4-bromo-2,6-dimethylinden-1-yl)propane,
- 2,2-bis(4-bromo-2-methyl-6-isopropylinden-1-yl)propane,
- 2,2-bis(4-bromo-2-methyl-6-fluoroinden-1-yl)propane,
- 2,2-bis(4-bromo-2-methyl-6-methoxyinden-1-yl)propane,
- 2,2-bis(4-bromo-2-methyl-6-dimethylaminoinden-1-yl)propane,
- 2,2-bis(4-bromo-2-methyl-6-diphenylphosphinoinden-1-yl)propane,
- 2,2-bis(4-bromo-2-methyl-6-methylsulfoinden-1-yl)propane,
- 2,2-bis(4-bromo-2-methyl-6-trimethylsilylinden-1-yl)propane,
- 2,2-bis(4-bromo-2-methyl-6-phenylinden-1-yl)propane,
- 2,2-bis(4-bromo-2-methyl-6-naphthylinden-1-yl)propane,
- 2,2-bis(4-bromo-2-methyl-6-N-indolylinden-1-yl)propane,
- 2,2-bis(4-bromo-2-methyl-6-trifluoromethylinden-1-yl)propane,
- 2,2-bis[4-bromo-2-methyl-6-(2-thienyl)inden-1-yl]propane,
- 2,2-bis[4-bromo-2-methyl-6-(4-pyridyl)inden-1-yl]propane,
- 2,2-bis(4-bromo-2-ethylinden-1-yl)propane,
- 2,2-bis(4-bromo-2-isopropylinden-1-yl)propane,
- 2,2-bis(4-bromo-2-phenylinden-1-yl)propane,
- 2-(4-bromo-2-methylinden-1-yl)-2-(4-chloro-2-methylinden-1-yl)propane,
- 2-(4-bromo-2-methylinden-1-yl)-2-(4-fluoro-2-methylinden-1-yl)propane,
- 2-(4-bromo-2-methylinden-1-yl)-2-(4-iodo-2-methylinden-1-yl)propane,
- 2-(4-bromo-2-methylinden-1-yl)-2-(2-methylinden-1-yl)propane,
- 2-(4-bromo-2-methylinden-1-yl)-2-(2-isopropylinden-1-yl)propane,
- 2-(4-bromo-2-methylinden-1-yl)-2-(inden-1-yl)propane,
- 2-(4-bromo-2-methylinden-1-yl)-2-(inden-2-yl)propane,
- 2-(4-bromo-2-methylinden-1-yl)-2-(2,4,6-trimethylinden-1-yl)propane,
- 2-(4-bromo-2-methylinden-1-yl)-2-(4-phenyl-2-methylinden-1-yl)propane,
- 2-(4-bromo-2-methylinden-1-yl)-2-(4-naphthyl-2-methylinden-1-yl)propane,
- 2-(4-bromo-2-methylinden-1-yl)-2-[4-(2,5-dimethylphenyl)-2-methylinden-1-yl]propane,
- 2-(4-bromo-2-methylinden-1-yl)-2-[4-(3,5-dimethylphenyl)-2-methylinden-1-yl]propane,
- 2-(4-bromo-2-methylinden-1-yl)-2-[4-(3,5-diisopropylphenyl)-2-methylinden-1-yl]propane,
- 2-(4-bromo-2-methylinden-1-yl)-2-[4-(3,5-di-tert-butylphenyl)-2-methylinden-1-yl]propane,
- 2-(4-bromo-2-methylinden-1-yl)-2-[4-(2-thienyl)-2-methylinden-1-yl]propane,
- 2-(4-bromo-2-methylinden-1-yl)-2-[4-(4-pyridyl)-2-methylinden-1-yl]propane,
- 2-(4-bromo-2-methylinden-1-yl)-2-(4-tert-butyl-2-methylinden-1-yl)propane,
- 2-(4-bromo-2-methylinden-1-yl)-2-(4-cyclohexyl-2-methylinden-1-yl)propane,
- 2-(4-bromo-2-methylinden-1-yl)-2-(4-isopropyl-2-methylinden-1-yl)propane,
- 2-(4-bromo-2-methylinden-1-yl)-2-(4-trimethysilyl-2-methylinden-1-yl)propane,
- 2-(4-bromo-2-methylinden-1-yl)-2-(4-trimethylgermyl-2-methylinden-1-yl)propane,
- 2-(4-bromo-2-methylinden-1-yl)-2-(4-methylthio-2-methylinden-1-yl)propane,
- 2-(4-bromo-2-methylinden-1-yl)-2-(4-diphenylphosphino-2-methylinden-1-yl)propane,
- 2-(4-bromo-2-methylinden-1-yl)-2-(4-trifluoromethyl-2-methylinden-1-yl)propane,
- 2-(4-bromo-2-methylinden-1-yl)-2-(cyclopentadienyl)propane,
- 2-(4-bromo-2-methylinden-1-yl)-2-(3-methylcyclopentadien-1-yl)propane,
- 2-(4-bromo-2-methylinden-1-yl)-2-(3-tert-butylcyclopentadien-1-yl)propane,
- 2-(4-bromo-2-methylinden-1-yl)-2-(3-trimethylsilylcyclopentadien-1-yl)propane,
- 2-(4-bromo-2-methylinden-1-yl)-2-(3-phenylcyclopentadien-1-yl)propane,
- 2-(4-bromo-2-methylinden-1-yl)-2-[3-(2-thienyl)cyclopentadien-1-yl]propane,
- 2-(4-bromo-2-methylinden-1-yl)-2-(3-diphenylphosphinocyclopentadien-1-yl)propane,
- 2-(4-bromo-2-methylinden-1-yl)-2-(2,3,4,5-tetramethylcyclopentadien-1-yl)propane,
- 2-(4-bromo-2-methylinden-1-yl)-2-(fluoren-9-yl)propane,
- 2-(4-bromo-2-methylinden-1-yl)-2-(3,6-dimethylfluoren-9-yl)propane,
- 2-(4-bromo-2-methylinden-1-yl)-2-(3,6-di-tert-butylfluoren-9-yl)propane,
- 2-(4-bromo-2-methylinden-1-yl)-2-(2,7-dibromofluoren-9-yl)propane,
- 2-(2-methylinden-1-yl)-2-(2,7-dibromofluoren-9-yl)propane,
- 2-(2-methylinden-1-yl)-2-(2,7-dichlorofluoren-9-yl)propane,
- 2-(2-methylinden-1-yl)-2-(2,7-diiodofluoren-9-yl)propane,
- 2-(2-methyl-4-phenylinden-1-yl)-2-(2,7-dibromofluoren-9-yl)propane,
- 2-(2,4-dimethylinden-1-yl)-2-(2,7-dibromofluoren-9-yl)propane,
- 2-(2-methyl-4-trimethylsilylinden-1-yl)-2-(2,7-dibromofluoren-9-yl)propane,
- 2-(2-methyl-4-tert-butylinden-1-yl)-2-(2,7-dibromofluoren-9-yl)propane,
- 2-(2-methyl-4-methoxyinden-1-yl)-2-(2,7-dibromofluoren-9-yl)propane,
- 2-(2-methyl-4-dimethylaminoinden-1-yl)-2-(2,7-dibromofluoren-9-yl)propane,
- 2-(2-methyl-4-trifluoromethylinden-1-yl)-2-(2,7-dibromofluoren-9-yl)propane,
- 2-(cyclopentadienyl)-2-(2,7-dibromofluoren-9-yl)propane,
- 2-(3-methylcyclopentadien-1-yl)-2-(2,7-dibromofluoren-9-yl)propane,
- 2-(3-tert-butylcyclopentadien-1-yl)-2-(2,7-dibromofluoren-9-yl)propane,
- 2-(3-phenylcyclopentadien-1-yl)-2-(2,7-dibromofluoren-9-yl)propane,
- 2-(3-trimethylsilylcyclopentadien-1-yl)-2-(2,7-dibromofluoren-9-yl)propane,
- 2-(3,4-dimethylcyclopentadien-1-yl)-2-(2,7-dibromofluoren-9-yl)propane,
- 2-[3-(2-thienyl)cyclopentadien-1-yl]-2-(2,7-dibromofluoren-9-yl)propane,
- 2-(fluoren-9-yl)-2-(2,7-dibromofluoren-9-yl)propane,
- 2-(3,6-dimethylfluoren-9-yl)-2-(2,7-dibromofluoren-9-yl)propane,
- 2-(3,6-ditertbutylfluoren-9-yl)-2-(2,7-dibromofluoren-9-yl)propane,
- 2-(3,6-diphenylfluoren-9-yl)-2-(2,7-dibromofluoren-9-yl)propane,
- 2,2-bis(4-bromo-2-methyl-5,6,7,8-tetrahydrocyclopenta[b]naphth-1-yl)propane,
- 2,2-bis(5-bromo-2-methyl-6,7,8,9-tetrahydrocyclopenta[a]naphth-3-yl)propane,
- 2,2-bis(4-bromo-2-methylcyclopenta[b]naphth-1-yl)propane,
- 2,2-bis(7-bromo-2,4-dimethylcyclopenta[b]naphth-1-yl)propane,
- 2,2-bis(8-bromo-6-methylindeno[5,6-d][1,3]dioxol-5-yl)propane,
- 2,2-bis(4-bromo-2,3,6-trimethylindeno[5,6-b]thien-7-yl)propane,
- 2,2-bis(2-bromo-4,6-dimethylindeno[5,6-b]thien-7-yl)propane,
- 2,2-bis(4-bromo-1,2,3,6-tetramethylcyclopenta[/]indol-7-yl)propane,
- 2,2-bis(4-bromo-1-phenyl-2,3,6-trimethylcyclopenta[f]indol-7-yl)propane,
- 2,2-bis(5-bromo-7-methylcyclopenta[g]quinol-8-yl)propane,
- 2,2-bis(2-bromo-5,7-dimethylcyclopenta[g]quinol-8-yl)propane,
- 2-(cyclopentadienyl)-2-(4-bromo-2-methyl-5,6,7,8-tetrahydrocyclopenta[b]naphth-1-yl)propane,
- 2-(cyclopentadienyl)-2-(5-bromo-2-methyl-6,7,8,9-tetrahydrocyclopenta[a]naphth-3-yl)propane,
- 2-(cyclopentadienyl)-2-(4-bromo-2-methylcyclopenta[b]naphth-1-yl)propane,
- 2-(cyclopentadienyl)-2-(7-bromo-2,4-dimethylcyclopenta[b]naphth-1-yl)propane,
- 2-(cyclopentadienyl)-2-(8-bromo-6-methylindeno[5,6-d][1,3]dioxol-5-yl)propane,
- 2-(cyclopentadienyl)-2-(4-bromo-2,3,6-trimethylindeno[5,6-b]thien-7-yl)propane,
- 2-(cyclopentadienyl)-2-(2-bromo-4,6-dimethylindeno[5,6-b]thien-7-yl)propane,
- 2-(cyclopentadienyl)-2-(4-bromo-1,2,3,6-tetramethylcyclopenta[f]indol-7-yl)propane,
- 2-(cyclopentadienyl)-2-(4-bromo-1-phenyl-2,3,6-trimethylcyclopenta[f]indol-7-yl)propane,
- 2-(cyclopentadienyl)-2-(4-bromocyclopenta[b]pyrid-7-yl)propane,
- 2-(cyclopentadienyl)-2-(5-bromo-7-methylcyclopenta[g]quinol-8-yl)propane,
- 2-(cyclopentadienyl)-2-(2-bromo-5,7-dimethylcyclopenta[g]quinol-8-yl)propane,
- 2-(inden-1-yl)-2-(4-bromo-2-methyl-5,6,7,8-tetrahydrocyclopenta[b]naphth-1-yl)propane,
- 2-(inden-1-yl)-2-(5-bromo-2-methyl-6,7,8,9-tetrahydrocyclopenta[a]naphth-3-yl)propane,
- 2-(inden-1-yl)-2-(4-bromo-2-methylcyclopenta[b]naphth-1-yl)propane,
- 2-(inden-1-yl)-2-(7-bromo-2,4-dimethylcyclopenta[b]naphth-1-yl)propane,
- 2-(inden-1-yl)-2-(8-bromo-6-methylindeno[5,6-d][1,3]dioxol-5-yl)propane,
- 2-(inden-1-yl)-2-(4-bromo-2,3,6-trimethylindeno[5,6-b]thien-7-yl)propane,
- 2-(inden-1-yl)-2-(2-bromo-4,6-dimethylindeno[5,6-b]thien-7-yl)propane,
- 2-(inden-1-yl)-2-(4-bromo-1,2,3,6-tetramethylcyclopenta[f]indol-7-yl)propane,
- 2-(inden-1-yl)-2-(4-bromo-1-phenyl-2,3,6-trimethylcyclopenta[/]indol-7-yl)propane,
- 2-(inden-1-yl)-2-(5-bromo-7-methylcyclopenta[g]quinol-8-yl)propane,
- 2-(inden-1-yl)-2-(2-bromo-5,7-dimethylcyclopenta[g]quinol-8-yl)propane,
- 2-(inden-2-yl)-2-(4-bromo-2-methyl-5,6,7,8-tetrahydrocyclopenta[b]naphth-1-yl)propane,
- 2-(inden-2-yl)-2-(5-bromo-2-methyl-6,7,8,9-tetrahydrocyclopenta[a]naphth-3-yl)propane,
- 2-(inden-2-yl)-2-(4-bromo-2-methylcyclopenta[b]naphth-1-yl)propane,
- 2-(inden-2-yl)-2-(7-bromo-2,4-dimethylcyclopenta[b]naphth-1-yl)propane,
- 2-(inden-2-yl)-2-(8-bromo-6-methylindeno[5,6-d[[1,3]dioxol-5-yl)propane,
- 2-(inden-2-yl)-2-(4-bromo-2,3,6-trimethylindeno[5,6-b]thien-7-yl)propane,
- 2-(inden-2-yl)-2-(2-bromo-4,6-dimethylindeno[5,6-b]thien-7-yl)propane,
- 2-(inden-2-yl)-2-(4-bromo-1,2,3,6-tetramethylcyclopenta[f]indol-7-yl)propane,
- 2-(inden-2-yl)-2-(4-bromo-1-phenyl-2,3,6-trimethylcyclopenta[f]indol-7-yl)propane,
- 2-(inden-2-yl)-2-(5-bromo-7-methylcyclopenta[g]quinol-8-yl)propane,
- 2-(inden-2-yl)-2-(2-bromo-5,7-dimethylcyclopenta[g]quinol-8-yl)propane,
- 2-(4-bromo-2-methylinden-1-yl)-2-(4-bromo-2-methyl-5,6,7,8-tetrahydrocyclopenta[b]naphth-1-yl)propane,
- 2-(4-bromo-2-methylinden-1-yl)-2-(5-bromo-2-methyl-6,7,8,9-tetrahydrocyclopenta[a]naphth-3-yl)propane,
- 2-(4-bromo-2-methylinden-1-yl)-2-(4-bromo-2-methylcyclopenta[b]naphth-1-yl)propane,
- 2-(4-bromo-2-methylinden-1-yl)-2-(7-bromo-2,4-dimethylcyclopenta[b]naphth-1-yl)propane,
- 2-(4-bromo-2-methylinden-1-yl)-2-(8-bromo-6-methylindeno[5,6-d][1,3]dioxol-5-yl)propane,
- 2-(4-bromo-2-methylinden-1-yl)-2-(4-bromo-2,3,6-trimethylindeno[5,6-b]thien-7-yl)propane,
- 2-(4-bromo-2-methylinden-1-yl)-2-(2-bromo-4,6-dimethylindeno[5,6-b]thien-7-yl)propane,
- 2-(4-bromo-2-methylinden-1-yl)-2-(4-bromo-1,2,3,6-tetramethylcyclopenta[f]indol-7-yl)propane,
- 2-(4-bromo-2-methylinden-1-yl)-2-(4-bromo-1-phenyl-2,3,6-trimethylcyclopenta[f]indol-7-yl)propane,
- 2-(4-bromo-2-methylinden-1-yl)-2-(5-bromo-7-methylcyclopenta[g]quinol-8-yl)propane,
- 2-(4-bromo-2-methylinden-1-yl)-2-(4-bromocyclopenta[b]pyrid-7-yl)propane,
- 2-(4-bromo-2-methylinden-1-yl)-2-(2-bromo-5,7-dimethylcyclopenta[g]quinol-8-yl)propane,
- 2-(fluoren-9-yl)-2-(4-bromo-2-methyl-5,6,7,8-tetrahydrocyclopenta[b]naphth-1-yl)propane,
- 2-(fluoren-9-yl)-2-(5-bromo-2-methyl-6,7,8,9-tetrahydrocyclopenta[a]naphth-3-yl)propane,
- 2-(fluoren-9-yl)-2-(4-bromo-2-methylcyclopenta[b]naphth-1-yl)propane,
- 2-(fluoren-9-yl)-2-(7-bromo-2,4-dimethylcyclopenta[b]naphth-1-yl)propane,
- 2-(fluoren-9-yl)-2-(8-bromo-6-methylindeno[5,6-d][1,3]dioxol-5-yl)propane,
- 2-(fluoren-9-yl)-2-(4-bromo-2,3,6-trimethylindeno[5,6-b]thien-7-yl)propane,
- 2-(fluoren-9-yl)-2-(2-bromo-4,6-dimethylindeno[5,6-b]thien-7-yl)propane,
- 2-(fluoren-9-yl)-2-(4-bromo-1,2,3,6-tetramethylcyclopenta[/]indol-7-yl)propane,
- 2-(fluoren-9-yl)-2-(4-bromo-1-phenyl-2,3,6-trimethylcyclopenta[/]indol-7-yl)propane,
- 2-(fluoren-9-yl)-2-(5-bromo-7-methylcyclopenta[g]quinol-8-yl)propane,
- 2-(fluoren-9-yl)-2-(2-bromo-5,7-dimethylcyclopenta[g]quinol-8-yl)propane,
- 1,2-bis(4-bromoinden-1-yl)ethane,
- 1,2-bis(4-bromoinden-2-yl)ethane,
- 1,2-(4-bromoinden-1-yl)(4-bromoinden-2-yl)ethane,
- 1,2-bis(4-chloro-2-methylinden-1-yl)ethane,
- 1,2-bis(4-iodo-2-methylinden-1-yl)ethane,
- 1,2-bis(4,6-dibromo-2-methylinden-1-yl)ethane,
- 1,2-bis(4-bromo-6-chloro-2-methylinden-1-yl)ethane,
- 1,2-bis(4-bromo-2,6-dimethylinden-1-yl)ethane,
- 1,2-bis(4-bromo-2-methyl-6-isopropylinden-1-yl)ethane,
- 1,2-bis(4-bromo-2-methyl-6-fluoroinden-1-yl)ethane,
- 1,2-bis(4-bromo-2-methyl-6-methoxyinden-1-yl)ethane,
- 1,2-bis(4-bromo-2-methyl-6-dimethylaminoinden-1-yl)ethane,
- 1,2-bis(4-bromo-2-methyl-6-diphenylphosphinoinden-1-yl)ethane,
- 1,2-bis(4-bromo-2-methyl-6-methylsulfoinden-1-yl)ethane,
- 1,2-bis(4-bromo-2-methyl-6-trimethylsilylinden-1-yl)ethane,
- 1,2-bis(4-bromo-2-methyl-6-phenylinden-1-yl)ethane,
- 1,2-bis(4-bromo-2-methyl-6-naphthylinden-1-yl)ethane,
- 1,2-bis(4-bromo-2-methyl-6-N-indolylinden-1-yl)ethane,
- 1,2-bis(4-bromo-2-methyl-6-trifluoromethylinden-1-yl)ethane,
- 1,2-bis[4-bromo-2-methyl-6-(2-thienyl)inden-1-yl]ethane,
- 1,2-bis[4-bromo-2-methyl-6-(4-pyridyl)inden-1-yl]ethane,
- 1,2-bis(4-bromo-2-ethylinden-1-yl)ethane,
- 1,2-bis(4-bromo-2-isopropylinden-1-yl)ethane,
- 1,2-bis(4-bromo-2-phenylinden-1-yl)ethane,
- 1-(4-bromo-2-methylinden-1-yl)-2-(4-chloro-2-methylinden-1-yl)ethane,
- 1-(4-bromo-2-methylinden-1-yl)-2-(4-fluoro-2-methylinden-1-yl)ethane,
- 1-(4-bromo-2-methylinden-1-yl)-2-(4-iodo-2-methylinden-1-yl)ethane,
- 1-(4-bromo-2-methylinden-1-yl)-2-(2-methylinden-1-yl)ethane,
- 1-(4-bromo-2-methylinden-1-yl)-2-(2-isopropylinden-1-yl)ethane,
- 1-(4-bromo-2-methylinden-1-yl)-2-(inden-1-yl)ethane,
- 1-(4-bromo-2-methylinden-1-yl)-2-(inden-2-yl)ethane,
- 1-(4-bromo-2-methylinden-1-yl)-2-(2,4,6-trimethylinden-1-yl)ethane,
- 1-(4-bromo-2-methylinden-1-yl)-2-(4-phenyl-2-methylinden-1-yl)ethane,
- 1-(4-bromo-2-methylinden-1-yl)-2-(4-naphthyl-2-methylinden-1-yl)ethane,
- 1-(4-bromo-2-methylinden-1-yl)-2-[4-(2,5-dimethylphenyl)-2-methylinden-1-yl]ethane,
- 1-(4-bromo-2-methylinden-1-yl)-2-[4-(3,5-dimethylphenyl)-2-methylinden-1-yl]ethane,
- 1-(4-bromo-2-methylinden-1-yl)-2-[4-(3,5-diisopropylphenyl)-2-methylinden-1-yl]ethane,
- 1-(4-bromo-2-methylinden-1-yl)-2-[4-(3,5-di-tert-butylphenyl)-2-methylinden-1-yl]ethane,
- 1-(4-bromo-2-methylinden-1-yl)-2-[4-(2-thienyl)-2-methylinden-1-yl]ethane,
- 1-(4-bromo-2-methylinden-1-yl)-2-[4-(4-pyridyl)-2-methylinden-1-yl]ethane,
- 1-(4-bromo-2-methylinden-1-yl)-2-(4-tert-butyl-2-methylinden-1-yl)ethane,
- 1-(4-bromo-2-methylinden-1-yl)-2-(4-cyclohexyl-2-methylinden-1-yl)ethane,
- 1-(4-bromo-2-methylinden-1-yl)-2-(4-isopropyl-2-methylinden-1-yl)ethane,
- 1-(4-bromo-2-methylinden-1-yl)-2-(4-trimethysilyl-2-methylinden-1-yl)ethane,
- 1-(4-bromo-2-methylinden-1-yl)-2-(4-trimethylgermyl-2-methylinden-1-yl)ethane,
- 1-(4-bromo-2-methylinden-1-yl)-2-(4-methylthio-2-methylinden-1-yl)ethane,
- 1-(4-bromo-2-methylinden-1-yl)-2-(4-diphenylphosphino-2-methylinden-1-yl)ethane,
- 1-(4-bromo-2-methylinden-1-yl)-2-(4-trifluoromethyl-2-methylinden-1-yl)ethane,
- 1-(4-bromo-2-methylinden-1-yl)-2-(cyclopentadienyl)ethane,
- 1-(4-bromo-2-methylinden-1-yl)-2-(3-methylcyclopentadien-1-yl)ethane,
- 1-(4-bromo-2-methylinden-1-yl)-2-(3-tert-butylcyclopentadien-1-yl)ethane,
- 1-(4-bromo-2-methylinden-1-yl)-2-(3-trimethylsilylcyclopentadien-1-yl)ethane,
- 1-(4-bromo-2-methylinden-1-yl)-2-(3-phenylcyclopentadien-1-yl)ethane,
- 1-(4-bromo-2-methylinden-1-yl)-2-[3-(2-thienyl)cyclopentadien-1-yl]ethane,
- 1-(4-bromo-2-methylinden-1-yl)-2-(3-diphenylphosphinocyclopentadien-1-yl)ethane,
- 1-(4-bromo-2-methylinden-1-yl)-2-(2,3,4,5-tetramethylcyclopentadien-1-yl)ethane,
- 1-(4-bromo-2-methylinden-1-yl)-2-(fluoren-9-yl)ethane,
- 1-(4-bromo-2-methylinden-1-yl)-2-(3,6-dimethylfluoren-9-yl)ethane,
- 1-(4-bromo-2-methylinden-1-yl)-2-(3,6-di-tert-butylfluoren-9-yl)ethane,
- 1-(4-bromo-2-methylinden-1-yl)-2-(2,7-dibromofluoren-9-yl)ethane,
- 1-(2-methylinden-1-yl)-2-(2,7-dibromofluoren-9-yl)ethane,
- 1-(2-methylinden-1-yl)-2-(2,7-dichlorofluoren-9-yl)ethane,
- 1-(2-methylinden-1-yl)-2-(2,7-diiodofluoren-9-yl)ethane,
- 1-(2-methyl-4-phenylinden-1-yl)-2-(2,7-dibromofluoren-9-yl)ethane,
- 1-(2,4-dimethylinden-1-yl)-2-(2,7-dibromofluoren-9-yl)ethane,
- 1-(2-methyl-4-trimethylsilylinden-1-yl)-2-(2,7-dibromofluoren-9-yl)ethane,
- 1-(2-methyl-4-tert-butylinden-1-yl)-2-(2,7-dibromofluoren-9-yl)ethane,
- 1-(2-methyl-4-methoxyinden-1-yl)-2-(2,7-dibromofluoren-9-yl)ethane,
- 1-(2-methyl-4-dimethylaminoinden-1-yl)-2-(2,7-dibromofluoren-9-yl)ethane,
- 1-(2-methyl-4-trifluoromethylinden-1-yl)-2-(2,7-dibromofluoren-9-yl)ethane,
- 1-(cyclopentadienyl)-2-(2,7-dibromofluoren-9-yl)ethane,
- 1-(3-methylcyclopentadien-1-yl)-2-(2,7-dibromofluoren-9-yl)ethane,
- 1-(3-tert-butylcyclopentadien-1-yl)-2-(2,7-dibromofluoren-9-yl)ethane,
- 1-(3-phenylcyclopentadien-1-yl)-2-(2,7-dibromofluoren-9-yl)ethane,
- 1-(3-trimethylsilylcyclopentadien-1-yl)-2-(2,7-dibromofluoren-9-yl)ethane,
- 1-(3,4-dimethylcyclopentadien-1-yl)-2-(2,7-dibromofluoren-9-yl)ethane,
- 1-[3-(2-thienyl)cyclopentadien-1-yl]-2-(2,7-dibromofluoren-9-yl)ethane,
- 1-(fluoren-9-yl)-2-(2,7-dibromofluoren-9-yl)ethane,
- 1-(3,6-dimethylfluoren-9-yl)-2-(2,7-dibromofluoren-9-yl)ethane,
- 1-(3,6-ditertbutylfluoren-9-yl)-2-(2,7-dibromofluoren-9-yl)ethane,
- 1-(3,6-diphenylfluoren-9-yl)-2-(2,7-dibromofluoren-9-yl)ethane,
- 1,2-bis(4-bromo-2-methyl-5,6,7,8-tetrahydrocyclopenta[b]naphth-1-yl)ethane,
- 1,2-bis(5-bromo-2-methyl-6,7,8,9-tetrahydrocyclopenta[a]naphth-3-yl)ethane,
- 1,2-bis(4-bromo-2-methylcyclopenta[b]naphth-1-yl)ethane,
- 1,2-bis(7-bromo-2,4-dimethylcyclopenta[b]naphth-1-yl)ethane,
- 1,2-bis(8-bromo-6-methylindeno[5,6-d][1,3]dioxol-5-yl)ethane,
- 1,2-bis(4-bromo-2,3,6-trimethylindeno[5,6-b]thien-7-yl)ethane,
- 1,2-bis(2-bromo-4,6-dimethylindeno[5,6-b]thien-7-yl)ethane,
- 1,2-bis(4-bromo-1,2,3,6-tetramethylcyclopenta[f]indol-7-yl)ethane,
- 1,2-bis(4-bromo-1-phenyl-2,3,6-trimethylcyclopenta[/]indol-7-yl)ethane,
- 1,2-bis(5-bromo-7-methylcyclopenta[g]quinol-8-yl)ethane,
- 1,2-bis(2-bromo-5,7-dimethylcyclopenta[g]quinol-8-yl)ethane,
- 1-(cyclopentadienyl)-2-(4-bromo-2-methyl-5,6,7,8-tetrahydrocyclopenta[b]naphth-1-yl)ethane,
- 1-(cyclopentadienyl)-2-(5-bromo-2-methyl-6,7,8,9-tetrahydrocyclopenta[a]naphth-3-yl)ethane,
- 1-(cyclopentadienyl)-2-(4-bromo-2-methylcyclopenta[b]naphth-1-yl)ethane,
- 1-(cyclopentadienyl)-2-(7-bromo-2,4-dimethylcyclopenta[b]naphth-1-yl)ethane,
- 1-(cyclopentadienyl)-2-(8-bromo-6-methylindeno[5,6-d][1,3]dioxol-5-yl)ethane,
- 1-(cyclopentadienyl)-2-(4-bromo-2,3,6-trimethylindeno[5,6-b]thien-7-yl)ethane,
- 1-(cyclopentadienyl)-2-(2-bromo-4,6-dimethylindeno[5,6-b]thien-7-yl)ethane,
- 1-(cyclopentadienyl)-2-(4-bromo-1,2,3,6-tetramethylcyclopenta[/]indol-7-yl)ethane,
- 1-(cyclopentadienyl)-2-(4-bromo-1-phenyl-2,3,6-trimethylcyclopenta[/]indol-7-yl)ethane,
- 1-(cyclopentadienyl)-2-(5-bromo-7-methylcyclopenta[g]quinol-8-yl)ethane,
- 1-(cyclopentadienyl)-2-(2-bromo-5,7-dimethylcyclopenta[g]quinol-8-yl)ethane,
- 1-(inden-1-yl)-2-(4-bromo-2-methyl-5,6,7,8-tetrahydrocyclopenta[b]naphth-1-yl)ethane,
- 1-(inden-1-yl)-2-(5-bromo-2-methyl-6,7,8,9-tetrahydrocyclopenta[a]naphth-3-yl)ethane,
- 1-(inden-1-yl)-2-(4-bromo-2-methylcyclopenta[b]naphth-1-yl)ethane,
- 1-(inden-1-yl)-2-(7-bromo-2,4-dimethylcyclopenta[b]naphth-1-yl)ethane,
- 1-(inden-1-yl)-2-(8-bromo-6-methylindeno[5,6-d][1,3]dioxol-5-yl)ethane,
- 1-(inden-1-yl)-2-(4-bromo-2,3,6-trimethylindeno[5,6-b]thien-7-yl)ethane,
- 1-(inden-1-yl)-2-(2-bromo-4,6-dimethylindeno[5,6-b]thien-7-yl)ethane,
- 1-(inden-1-yl)-2-(4-bromo-1,2,3,6-tetramethylcyclopenta[f]indol-7-yl)ethane,
- 1-(inden-1-yl)-2-(4-bromo-1-phenyl-2,3,6-trimethylcyclopenta[f]indol-7-yl)ethane,
- 1-(inden-1-yl)-2-(5-bromo-7-methylcyclopenta[g]quinol-8-yl)ethane,
- 1-(inden-1-yl)-2-(2-bromo-5,7-dimethylcyclopenta[g]quinol-8-yl)ethane,
- 1-(inden-2-yl)-2-(4-bromo-2-methyl-5,6,7,8-tetrahydrocyclopenta[b]naphth-1-yl)ethane,
- 1-(inden-2-yl)-2-(5-bromo-2-methyl-6,7,8,9-tetrahydrocyclopenta[a]naphth-3-yl)ethane,
- 1-(inden-2-yl)-2-(4-bromo-2-methylcyclopenta[b]naphth-1-yl)ethane,
- 1-(inden-2-yl)-2-(7-bromo-2,4-dimethylcyclopenta[b]naphth-1-yl)ethane,
- 1-(inden-2-yl)-2-(8-bromo-6-methylindeno[5,6-d][1,3]dioxol-5-yl)ethane,
- 1-(inden-2-yl)-2-(4-bromo-2,3,6-trimethylindeno[5,6-b]thien-7-yl)ethane,
- 1-(inden-2-yl)-2-(2-bromo-4,6-dimethylindeno[5,6-b]thien-7-yl)ethane,
- 1-(inden-2-yl)-2-(4-bromo-1,2,3,6-tetramethylcyclopenta[f]indol-7-yl)ethane,
- 1-(inden-2-yl)-2-(4-bromo-1-phenyl-2,3,6-trimethylcyclopenta[f]indol-7-yl)ethane,
- 1-(inden-2-yl)-2-(5-bromo-7-methylcyclopenta[g]quinol-8-yl)ethane,
- 1-(inden-2-yl)-2-(2-bromo-5,7-dimethylcyclopenta[g]quinol-8-yl)ethane,
- 1-(4-bromo-2-methylinden-1-yl)-2-(4-bromo-2-methyl-5,6,7,8-tetrahydrocyclopenta[b]naphth-1-yl)ethane,
- 1-(4-bromo-2-methylinden-1-yl)-2-(5-bromo-2-methyl-6,7,8,9-tetrahydrocyclopenta[a]naphth-3-yl)ethane,
- 1-(4-bromo-2-methylinden-1-yl)-2-(4-bromo-2-methylcyclopenta[b]naphth-1-yl)ethane,
- 1-(4-bromo-2-methylinden-1-yl)-2-(7-bromo-2,4-dimethylcyclopenta[b]naphth-1-yl)ethane,
- 1-(4-bromo-2-methylinden-1-yl)-2-(8-bromo-6-methylindeno[5,6-d][1,3]dioxol-5-yl)ethane,
- 1-(4-bromo-2-methylinden-1-yl)-2-(4-bromo-2,3,6-trimethylindeno[5,6-b]thien-7-yl)ethane,
- 1-(4-bromo-2-methylinden-1-yl)-2-(2-bromo-4,6-dimethylindeno[5,6-b]thien-7-yl)ethane,
- 1-(4-bromo-2-methylinden-1-yl)-2-(4-bromo-1,2,3,6-tetramethylcyclopenta[/]indol-7-yl)ethane,
- 1-(4-bromo-2-methylinden-1-yl)-2-(4-bromo-1-phenyl-2,3,6-trimethylcyclopenta[f]indol-7-yl)ethane,
- 1-(4-bromo-2-methylinden-1-yl)-2-(5-bromo-7-methylcyclopenta[g]quinol-8-yl)ethane,
- 1-(4-bromo-2-methylinden-1-yl)-2-(2-bromo-5,7-dimethylcyclopenta[g]quinol-8-yl)ethane,
- 1-(fluoren-9-yl)-2-(4-bromo-2-methyl-5,6,7,8-tetrahydrocyclopenta[b]naphth-1-yl)ethane,
- 1-(fluoren-9-yl)-2-(5-bromo-2-methyl-6,7,8,9-tetrahydrocyclopenta[a]naphth-3-yl)ethane,
- 1-(fluoren-9-yl)-2-(4-bromo-2-methylcyclopenta[b]naphth-1-yl)ethane,
- 1-(fluoren-9-yl)-2-(7-bromo-2,4-dimethylcyclopenta[b]naphth-1-yl)ethane,
- 1-(fluoren-9-yl)-2-(8-bromo-6-methylindeno[5,6-d][1,3]dioxol-5-yl)ethane,
- 1-(fluoren-9-yl)-2-(4-bromo-2,3,6-trimethylindeno[5,6-b]thien-7-yl)ethane,
- 1-(fluoren-9-yl)-2-(2-bromo-4,6-dimethylindeno[5,6-b]thien-7-yl)ethane,
- 1-(fluoren-9-yl)-2-(4-bromo-1,2,3,6-tetramethylcyclopenta[f]indol-7-yl)ethane,
- 1-(fluoren-9-yl)-2-(4-bromo-1-phenyl-2,3,6-trimethylcyclopenta[/]indol-7-yl)ethane,
- 1-(fluoren-9-yl)-2-(4-bromocyclopenta[b]pyrid-7-yl)ethane,
- 1-(fluoren-9-yl)-2-(5-bromo-7-methylcyclopenta[g]quinol-8-yl)ethane,
- 1-(fluoren-9-yl)-2-(2-bromo-5,7-dimethylcyclopenta[g]quinol-8-yl)ethane,
- 1,2-bis[2-(4-bromo-3-dimethylamino-1,3-benzothiaborollide)]ethane,
- 1,2-bis(4-bromo-3a,7a-azaborinden-1-yl)ethane,
- 1,2-bis[3-(7-bromo-2-dimethylamino-1,2-benzothiaborolide)]ethane,
- 1,2-bis[5-(3-bromo-2-dimethylamino-1,2-thiaborollide)]ethane,
- 1-(cyclopentadienyl)-2-[2-(4-bromo-3-dimethylamino-1,3-benzothiaborollide)]ethane,
- 1-(cyclopentadienyl)-2-(4-bromo-3a,7a-azaborinden-1-yl)ethane,
- 1-(cyclopentadienyl)-2-[3-(7-bromo-2-dimethylamino-1,2-benzothiaborollide)]ethane,
- 1-(cyclopentadienyl)-2-[5-(3-bromo-2-dimethylamino-1,2-thiaborollide)]ethane,
- 1-(inden-1-yl)-2-[2-(4-bromo-3-dimethylamino-1,3-benzothiaborollide)]ethane,
- 1-(inden-1-yl)-2-(4-bromo-3a,7a-azaborinden-1-yl)ethane,
- 1-(inden-1-yl)-2-[3-(7-bromo-2-dimethylamino-1,2-benzothiaboralide-3)]ethane,
- 1-(inden-1-yl)-2-[5-(3-bromo-2-dimethylamino-1,2-thiaborollide)]ethane,
- 1-(inden-2-yl)-2-[2-(4-bromo-3-dimethylamino-1,3-benzothiaborollide)]ethane,
- 1-(inden-2-yl)-2-(4-bromo-3a,7a-azaborinden-1-yl)ethane,
- 1-(inden-2-yl)-2-[3-(7-bromo-2-dimethylamino-1,2-benzothiaborollide)]ethane,
- 1-(inden-2-yl)-2-[5-(3-bromo-2-dimethylamino-1,2-thiaborollide)]ethane,
- 1-(fluoren-9-yl)-2-[2-(4-bromo-3-dimethylamino-1,3-benzothiaborollide)]ethane,
- 1-(fluoren-9-yl)-2-(4-bromo-3a,7a-azaborinden-1-yl)ethane,
- 1-(fluoren-9-yl)-2-[3-(7-bromo-2-dimethylamino-1,2-benzothiaborolide)]ethane, and
- 1-(fluoren-9-yl)-2-[5-(3-bromo-2-dimethylamino-1,2-thiaborollide]ethane.
- Starting materials of the formula (I) used in the synthetic process of the present invention can be synthesized in a simple manner by customary methods of the prior art (Metallocenes: Synthesis, Reactivity, Applications, Ed. by A. Togni, R. L. Halterman.—Wiley-VCH, 1998). For instance, deprotonation of halo-substituted indene followed by treatment with R2SiCl2 gives bis-indenyl ligands with R2Si bridge in position 1 of indenyls (WO 9840331). The respective compounds with CR2 bridge can be readily prepared, for example, by the nucleophilic addition of the haloindenyl anion to fulvenes (WO 2004087775).
- Aliphatic, heteroaliphatic, aromatic, heteroaromatic, alkenyl, and heteroalkenyl organometallic compounds of the formula (III) are likewise obtainable in a simple manner by standard methods of the prior art or can be purchased commercially. The synthesis of organozinc reagents, of importance in Negishi reactions, is described, for example, in Organozinc Reagents, Ed. by P. Knochel, P. Jones, Oxford U Press, 1999. The synthesis of boronic acids, of importance in Suzuki-Miyaura reactions, is described, for example, in Organic Synthesis, Collective Volume IV, Wiley, 1963. The synthesis of organotin reagents, of importance in Stille reactions, is described, for example, in V. Farina, V. Krishnamurthy, W. J. Scott, The Stille Reaction, Wiley, 1998 and the references cited therein. The synthesis of other organometallic reagents of the formula (III) involves standard methods of organometallic chemistry and is described, for example, in Organometallics in Synthesis, Ed. By M. Schlosser, and in J. March, Advanced Organic Chemistry, 4th Edition, 1992 and the references cited therein.
- The synthesis of chelating ligands of the formula (II) which are substituted by hydrocarbyl groups in the six-membered ring of indenes and heteroindenes or in the five-membered heterocyclic ring of cyclopentathiophenes and related fragments is carried out by means of a transition metal-catalyzed sp2-sp3 and sp2-sp2 coupling reaction of halo-substituted chelating ligands of the formula (I) with organometallic reagents of the formula (III). These reactions are carried out in suitable solvents, such as diethyl ether, tetrahydrofuran, toluene, etc., under an inert gas atmosphere. In principle, it is possible to use transition metal complexes of Groups 8 to 10 of the Periodic Table of the Elements, preferably Group 10. Particularly useful complexes are complexes of nickel and palladium. Non-limiting examples of transition metal catalysts include: palladium chloride, palladium bromide, palladium iodide, palladium dibenzylidenacetone, palladium acetate, dichlorobis(triphenylphosphine)palladium, bis(tri-tert-butylphosphine)palladium, dichlorobis(triphenylphosphine)palladium(II), polymer-bound catalysts such as dichlorobis(triphenylphosphine)palladium(II) polymer bound or tetrakis(triphenylphosphine)palladium(0) polymer bound (both are available from Aldrich Chemical Company where the polymer is a divinylbenzene crosslinked polystyrene), nickel chloride, nickel bromide, nickel iodide, nickel acetylacetonate, dichlorobis(triphenylphosphine)nickel, bis(1,5-cyclooctadienyl)nickel, bis(cyclopentadienyl)nickel.
- Alternatively, the catalyst can be a mixture of one or more of the above mentioned salts and a suitable ligand. This combination can considerably increase the yield of the target products of the cross-coupling reactions. Non-limiting examples of such ligands (which may be polymer-supported) include: trimethylphosphine, triethylphosphine, triisopropylphosphine, tri(tert-butyl)phosphine, tricyclohexylphosphine, triphenylphosphine, tri(o-tolyl)phosphine, (2-biphenyl)di(tert-butyl)phosphine, (2′-dimethylaminobiphenyl-2)di(tert-butyl)phosphine, (9-phenanthrenyl)dicyclohexylphosphine, 1.1′-bis(di-tert-butylphosphino)ferrocene, XANTPHOS, DPEPHOS, 2,2′-bipyridyl, o-phenanthroline, 1,1′-bis(diphenylphosphino)ferrocene, mtrimethylphosphite, triethylphosphite, triisopropylphosphite, triphenylphosphite, tricyclohexylphosphite, tribenzylphosphite as well as carbine ligand of the following formula:
Examples of commercially available polymeric bound phosphines include poly(ethylene glycol)triphenylphosphine; and dicyclohexylphenylphosphine, polymer-bound; (4-hydroxyphenyl)diphenylphosphine, polymer-bound; triphenylphosphine, polymer-supported; R-(+)-2,2′-bis(diphenylphosphino)-1,1′-binaphthalene, polymer-bound; S-(−)-2,2′-bis(diphenylphosphino)-1,1′-binaphthalene, polymer-bound (all available from Aldrich Chemical Company where the polymer-bound or polymer-supported is a divinylbenzene crosslinked polystyrene). - The most preferred ligands for nickel catalyst are: triphenylphosphine, triethylphosphite; 2,2′-bipyridyl and o-phenanthroline. The most preferred ligands for palladium catalyst are: tri(tert-butyl)phosphine, (2-biphenyl)di(tert-butyl)phosphine, (2′-dimethylaminobiphenyl-2)di(tert-butyl)phosphine, (9-phenanthrenyl)dicyclohexylphosphine, 1.1′-bis(di-tert-butylphosphino)ferrocene, XANTPHOS, and the carbene ligand shown above.
- Different cross-coupling reactions can be used to functionalize the starting chelating ligands of the formula (I) to obtain the cross-coupling products of the formula (II). The general protocols for the Kumada reaction using Grignard reagents, the Suzuki reaction using organoboron compounds, particularly NaBPh4, boronic acids and their ethers, the Negishi reaction using organozinc compounds, the Stille reaction using organotin derivatives, and other cross-coupling reactions are described in Metal-Catalyzed Cross-Coupling Reactions, Ed. by F. Diederich, P. J. Stang, Wiley, 1998 and the references cited therein.
- Non-limiting examples of Grignard reagents of the formula (III) which are preferred in the process of the present invention include: methylmagnesium chloride, methylmagnesium bromide, methylmagnesium iodide, dimethylmagnesium, ethylmagnesium bromide, n-propylmagnesium chloride, isopropylmagnesium chloride, n-butylmagnesium chloride, sec-butylmagnesium chloride, isobutylmagnesium chloride, tert-butylmagnesium chloride, cyclopentylmagnesium chloride, cyclohexylmagnesium chloride, benzylmagnesium chloride, 4-methylbenzylmagnesium chloride, 4-methoxybenzylmagnesium chloride, 4-trifluoromethyhnagnesium chloride, diphenylmethylmagnesium bromide, adamantylmagnesum bromide, cyclohexenylmagnesium chloride, isopropenylmagnesium chloride, 2-phenylethenylmagnesium bromide, trimethylsilylmethylmagnesium chloride, neopentylmagnesium chloride, methoxymethylmagnesium chloride, 3-methoxypropylmagnesium chloride, dimethylaminomethylmagnesium chloride, diphenylphosphinomethylmagnesium chloride, 2-pyridylmagnesium bromide, 4-pyridylmagnesium chloride, 2-thienylmagnesium bromide, 2-benzothienylmagnesium bromide, 2-benzofurylmagnesium chloride, 3-(N-methylindolyl)magnesium bromide, phenylmagnesium bromide, 2-methylphenylmagnesium bromide, 3-methylphenylmagnesium bromide, 4-methylphenylmagnesium bromide, 4-tert-butylphenylmagnesium bromide, 2,6-dimethylphenylmagnesium bromide, 2,6-diisopropylphenylmagnesium bromide, 3,5-dimethylphenylmagnesium chloride, 2,5-dimethylphenylmagnesium chloride, 3,5-diisopropylphenylmagnesium chloride, 3,5-tert-butylphenylmagnesium chloride, 2-isopropylphenylmagnesium chloride, 3-trifluoromethylphenylmagnesium chloride, 4-fluorophenylmagnesium chloride, 4-methoxyphenylmagnesium chloride, 2-methoxyphenylmagnesium chloride, 4-dimethylaminophenylmagnesium chloride, 1-naphthylmagnesium chloride, 2-naphthylmagnesium chloride, and pentafluorophenylmagnesium bromide.
- The most preferred Grignard reagents are: cyclopentylmagnesium chloride, cyclohexylmagnesium chloride, 2-thienylmagnesium bromide, 3,5-dimethylphenylmagnesium chloride, 2,5-dimethylphenylmagnesium chloride, 3,5-diisopropylphenylmagnesium chloride, 3,5-tert-butylphenylmagnesium chloride, 1-naphthylmagnesium chloride.
- Non-limiting examples of organozinc reagents of the formula (III) which are preferred in the process of the present invention include: methylzinc chloride, methylzinc bromide, methylzinc iodide, dimethylzinc, ethylzinc bromide, n-propylzinc chloride, isopropylzinc chloride, n-butylzinc chloride, sec-butylzinc chloride, isobutylzinc chloride, tert-butylzinc chloride, cyclopentylzinc chloride, cyclohexylzinc chloride, benzylzinc chloride, 4-methylbenzylzinc chloride, 4-methoxybenzylzinc chloride, 4-trifluoromethylzinc chloride, diphenylmethylzinc bromide, adamantylmagnesum bromide, cyclohexenylzinc chloride, isopropenylzinc chloride, 2-phenylethenylzinc bromide, trimethylsilylmethylzinc chloride, neopentylzinc chloride, methoxymethylzinc chloride, 3-methoxypropylzinc chloride, dimethylaminomethylzinc chloride, diphenylphosphinomethylzinc chloride, 2-pyridylzinc bromide, 4-pyridylzinc chloride, 2-thienylzinc bromide, 2-benzothienylzinc bromide, 2-benzofurylzinc chloride, 3-(N-methylindolyl)zinc bromide, phenylzinc bromide, 2-methylphenylzinc bromide, 3-methylphenylzinc bromide, 4-methylphenylzinc bromide, 4-tert-butylphenylzinc bromide, 2,6-dimethylphenylzinc bromide, 2,6-diisopropylphenylzinc bromide, 3,5-dimethylphenylzinc chloride, 2,5-dimethylphenylzinc chloride, 3,5-diisopropylphenylzinc chloride, 3,5-tert-butylphenylzinc chloride, 2-isopropylphenylzinc chloride, 3-trifluoromethylphenylzinc chloride, 4-fluorophenylzinc chloride, 4-methoxyphenylzinc chloride, 2-methoxyphenylzinc chloride, 4-dimethylaminophenylzinc chloride, 1-naphthylzinc chloride, 2-naphthylzinc chloride, 4-cyanophenylzinc bromide, 4-carboethoxyphenylzinc iodide, pentafluorophenylzinc bromide.
- The most preferred organozinc reagents are: cyclopentylzinc chloride, cyclohexylzinc chloride, 2-thienylzinc bromide, 3,5-dimethylphenylzinc chloride, 2,5-dimethylphenylzinc chloride, 3,5-diisopropylphenylzinc chloride, 3,5-tert-butylphenylzinc chloride, 1-naphthylzinc chloride.
- Non-limiting examples of organoboron reagents of the formula (III) which are preferred in the process of the present invention are: methylboronic acid, ethylboronic acid, n-propylboronic acid, isopropylboronic acid, n-butylboronic acid, sec-butylboronic acid, isobutylboronic acid, tert-butylboronic acid, cyclopentylboronic acid, cyclohexylboronic acid, benzylboronic acid, 4-methylbenzylboronic acid, 4-methoxybenzylboronic acid, 4-trifluoromethylboronic acid, diphenylmethylboronic acid, adamantylboronic acid, cyclohexenylboronic acid, isopropenylboronic acid, 2-phenylethenylboronic acid, trimethylsilylmethylboronic acid, neopentylboronic acid, methoxymethylboronic acid, 3-methoxypropylboronic acid, dimethylaminomethylboronic acid, diphenylphosphinomethylboronic acid, 2-pyridylboronic acid, 4-pyridylboronic acid, 2-thienylboronic acid, 2-benzothienylboronic acid, 2-benzofurylboronic acid, 3-(N-methylindolyl)boronic acid, phenylboronic acid, sodium tetraphenylborate, 4,4,5,5-tetramethyl-2-phenyl-1,3,2-dioxaborolane, 2-phenyl-1,3,2-benzodioxaborole, triphenylboron, 2-methylphenylboronic acid, 3-methylphenylboronic acid, 4-methylphenylboronic acid, 4-tert-butylphenylboronic acid, 2,6-dimethylphenylboronic acid, 2,6-diisopropylphenylboronic acid, 3,5-dimethylphenylboronic acid, 2,5-dimethylphenylboronic acid, 3,5-diisopropylphenylboronic acid, 3,5-tert-butylphenylboronic acid, 2-isopropylphenylboronic acid, 3-trifluoromethylphenylboronic acid, 4-fluorophenylboronic acid, 4-methoxyphenylboronic acid, 2-methoxyphenylboronic acid, 4-dimethylaminophenylboronic acid, 1-naphthylboronic acid, 2-naphthylboronic acid, 4-cyanophenylboronic acid, 4-carboethoxyphenylboronic acid, pentafluorophenylboronic acid.
- The most preferred organoboron reagents are: 2-thienylboronic acid, 3,5-dimethylphenylboronic acid, 2,5-dimethylphenylboronic acid, 3,5-diisopropylphenylboronic acid, 3,5-tert-butylphenylboronic acid, 1-naphthylboronic acid.
- The cross-coupling reactions using organoboron reagents (Suzuki reaction) require a base in addition to NaBPh4. Non-limiting examples of bases to be used include: potassium carbonate, sodium carbonate, lithium carbonate, cesium carbonate, rubidium carbonate, lithium hydroxide, sodium hydroxide, potassium hydroxide, sodium triphosphate, potassium triphosphate, sodium hydrocarbonate, calcium carbonate, calcium oxide, barium carbonate, barium oxide, aluminium carbonate, aluminium oxide, yttrium carbonate, yttrium oxide, cerium carbonate, cerium oxide, barium hydroxide, calcium hydroxide, yttrium hydroxide, cerium hydroxide, aluminium hydroxide, sodium methylate, sodium ethylate, sodium isopropylate, sodium n-butoxide, sodium tert-butoxide, lithium ethylate, potassium ethylate.
- Non-limiting examples of organotin reagents of the formula (III) which are preferred in the process of the present invention include: tetramethyltin, teraethyltin, tetracyclohexyltin, 2-pyridyl-tri-n-butyltin, 4-pyridyl-tri-n-butyltin, 2-thienyl-tri-n-butyltin, 2-benzothienyl-tri-n-butyltin, 2-benzofuryl-tri-n-butyltin, 3-(N-methylindolyl)-tri-n-butyltin, phenyl-tri-n-butyltin, phenyltrimethyltin, phenyltriethyltin, phenyltriisopropyltin, phenyltriisobutyltin, phenyltricyclohexyltin, tetraphenyltin, 2-methylphenyl-tri-n-butyltin, 3-methylphenyl-tri-n-butyltin, 4-methylphenyl-tri-n-butyltin, 4-tert-butylphenyl-tri-n-butyltin, 2,6-dimethylphenyl-tri-n-butyltin, 2,6-diisopropylphenyl-tri-n-butyltin, 3,5-dimethylphenyl-tri-n-butyltin, 2,5-dimethylphenyl-tri-n-butyltin, 3,5-diisopropylphenyl-tri-n-butyltin, 3,5-tert-butylphenyl-tri-n-butyltin, 2-isopropylphenyl-tri-n-butyltin, 3-trifluoromethylphenyl-tri-n-butyltin, 4-fluorophenyl-tri-n-butyltin, 4-methoxyphenyl-tri-n-butyltin, 2-methoxyphenyl-tri-n-butyltin, 4-dimethylaminophenyl-tri-n-butyltin, 1-naphthyl-tri-n-butyltin, 2-naphthyl-tri-n-butyltin, 4-cyanophenyl-tri-n-butyltin, 4-carboethoxyphenyl-tri-n-butyltin, pentafluorophenyl-tri-n-butyltin, phenyltin trichloride, phenyltin tribromide, phenyltin triiodide, phenyltin trifluoride, phenyltin triethoxyde.
- The most preferred organotin reagents are: 2-thienyl-tri-n-butyltin, 3,5-dimethylphenyl-tri-n-butyltin, 2,5-dimethylphenyl-tri-n-butyltin, 3,5-diisopropylphenyl-tri-n-butyltin, 3,5-tert-butylphenyl-tri-n-butyltin, 1-naphthyl-tri-n-butyltin.
- The cross-coupling reactions using organotin reagents (Stille reaction) require the use of a nucleophilic aid agent. Non-limiting examples of such aiding agents to be used include: lithium fluoride, sodium fluoride, potassium fluoride, rubidium fluoride, cesium fluoride, tetramethylammonium fluoride, tetraethylammonium fluoride, tetra-n-butylammonium fluoride, magnesium fluoride, calcium fluoride, barium fluoride, aluminium fluoride, tetramethylphosphonium fluoride, lithium chloride, sodium bromide, potassium chloride, rubidium chloride, cesium chloride, tetramethylammonium chloride, tetraethylammonium chloride, tetra-n-butylammonium chloride, magnesium chloride, calcium chloride, barium chloride, aluminium chloride, tetramethylphosphonium chloride, lithium hydroxide, sodium hydroxide, potassium hydroxide, rubidium hydroxide, cesium hydroxide, tetramethylammonium hydroxide, tetraethylammonium hydroxide, tetra-n-butylammonium hydroxide, magnesium hydroxide, calcium hydroxide, barium hydroxide, aluminium hydroxide, tetramethylphosphonium hydroxide, lithium methoxide, sodium methoxide, potassium methoxide, rubidium methoxide, cesium methoxide, magnesium methoxide, calcium methoxide, barium methoxide, aluminium methoxide, sodium ethoxide, sodium n-propoxide, sodium isopropoxide, sodium n-butoxide, sodium isobutoxide, sodium sec-butoxide, sodium phenoxide.
- Non-limiting examples of organometallic compounds of the formula (III), other than Grignard, organozinc, organoboron, and organotin reagents, include: dimethylcadmium, diphenylcadmium, trimethylindium, tripenylindium, phenylindium dichloride, trimethylgallium, triphenylgallium, phenylgallium dichloride, tetraphenylsilane, phenyltrichlorosilane, phenyltrimethoxysilane, tetraphenylgermane, phenyltrichlorogermane, phenyltrimethoxygermane, triphenylbismuth, phenylbismuth dichloride, phenylbismuth diethoxide.
- In most cases it is sufficient to use the particularly preferred catalyst NiCl2(dppp)2 or NiCl2(PPh3)2 in an amount of 0.01 to 5 mol %, preferably 1 to 3 mol % and most preferably about 2 mol %, in each case relative to the chelating ligand of the formula (I) used. Analogously, in most cases it is sufficient to use the particularly preferred catalyst Pd(OAc)2 in combination with a phosphine or phosphine ligand such as ligands A through N, or Pd(PtBu3)2 in an amount of 0.000001 to 5 mol %, preferably 0.01 to 2 mol % and most preferably about 1 mol %, in each case based on the chelating ligand of the formula (I) used. OAc is O2CCH3.
- Suitable solvents for the metal-catalyzed cross-coupling of chelating ligands of the formula (I) with organometallic reagents of the formula (III) are, for example, aliphatic ethers such as diethyl ether, dibutyl ether, methyl tert-butyl ether, tetrahydrofuran, dioxane and dimethoxyethane, aliphatic hydrocarbons such as pentane, hexane and the like, aromatic hydrocarbons such as benzene, toluene, xylenes and the like. In many cases, other solvents can be used, such as dimethylformamide, water, acetone and the like. Mixtures of various solvents in various mixing ratios can also be used according to the present invention to match the solubility of the starting materials and end products to the reaction conditions in an optimal fashion. It should be noted that protic solvents such as water, alcohols and their mixtures with aprotic solvents can be also be used, but only in the case of Suzuki reactions involving starting materials (I) where the bridging group B is not SiR2, GeR2, SiR2—SiR2, GeR2—GeR2, BR, BR—BR and the like, since these groups are labile in the presence of the transition-metal catalyst in protic solvents.
- A person skilled in the art will choose solvents or solvent mixtures appropriate to the specific substitution pattern of the starting compounds and the catalysts and reagents used by means of simple tests or on the basis of known solubilities and solvent properties.
- In preferred embodiments of the process of the present invention, the chelating ligand of the formula (I) together with a sufficient amount of solvent are placed in the reaction vessel under an inert atmosphere. The catalyst, an optional ligand and an optional base or nucleophilic aid agent are subsequently added followed by the addition of a solution of the organometallic compound of the formula (III) in a suitable solvent at room or lower (−78° C. to +10° C.) temperatures. The cross-coupling reaction can be carried out by vigorous stirring at room or elevated temperatures depending on the reaction under study, the reagents and the catalyst used. Addition of the reagents, catalyst and other additives can be performed in different orders. A person skilled in the art will choose an appropriate procedure depending on the reactivity and substitution of the individual reagents.
- Non-limiting preferred examples of the chelating ligands of the formula (II), where R is hydrocarbyl, substituted hydrocarbyl, halocarbyl, or substituted halocarbyl, which can be prepared according to the present invention include:
- bis(4-R-2-methylinden-1-yl)dimethylsilane,
- bis(4-R-2-inden-1-yl)dimethylsilane,
- (4-R-inden-1-yl)(4-chloroinden-1-yl)dimethylsilane,
- (4-R-inden-1-yl)(4-bromoinden-1-yl)dimethylsilane,
- (4-R-inden-1-yl)(4-iodoinden-1-yl)dimethylsilane,
- bis(4-R-inden-1-yl)dimethylsilane,
- bis(4-R-inden-2-yl)dimethylsilane,
- (4-R-inden-1-yl)(4-R-inden-2-yl)dimethylsilane,
- bis(4-R-2-methylinden-1-yl)diethylsilane,
- bis(4-R-2-methylinden-1-yl)methylphenylsilane,
- bis(4-R-2-methylinden-1-yl)diphenylsilane,
- bis(4-R-2-methylinden-1-yl)dimethylgermane,
- bis(4-R-2-methylinden-1-yl)phenylphosphine,
- bis(4-R-2-methylinden-1-yl)methylphosphine,
- bis(4-R-2-methylinden-1-yl)isopropylphosphine,
- 1,2-bis(4-R-2-methylinden-1-yl)-1′,1″,2′,2″-tetramethyldisilane,
- 1,2-bis(4-R-2-methylinden-1-yl)ethane,
- cis-1,2-bis(4-R-2-methylinden-1-yl)ethylene,
- bis(4-R-2-methylinden-1-yl)methane,
- 2,2′-bis(4-R-2-methylinden-1-yl)propane,
- bis(4-R-2-methylinden-1-yl)diphenylmethane,
- bis(4,6-di-2-methylinden-1-yl)dimethylsilane,
- bis(4-R-2,6-dimethylinden-1-yl)dimethylsilane,
- bis(4-R-2-methyl-6-isopropylinden-1-yl)dimethylsilane,
- bis(4-R-2-methyl-6-methoxyinden-1-yl)dimethylsilane,
- bis(4-R-2-methyl-6-dimethylaminoinden-1-yl)dimethylsilane,
- bis(4-R-2-methyl-6-diphenylphosphinoinden-1-yl)dimethylsilane,
- bis(4-R-2-methyl-6-methylsulfoinden-1-yl)dimethylsilane,
- bis(4-R-2-methyl-6-trimethylsilylinden-1-yl)dimethylsilane,
- bis(4-R-2-methyl-6-phenylinden-1-yl)dimethylsilane,
- bis(4-R-2-methyl-6-naphthylinden-1-yl)dimethylsilane,
- bis(4-R-2-methyl-6-N-indolylinden-1-yl)dimethylsilane,
- bis(4-R-2-methyl-6-trifluoromethylinden-1-yl)dimethylsilane,
- bis[4-R-2-methyl-6-(2-thienyl)inden-1-yl]dimethylsilane,
- bis[4-R-2-methyl-6-(4-pyridyl)inden-1-yl]dimethylsilane,
- bis(4-R-2-ethylinden-1-yl)dimethylsilane,
- bis(4-R-2-isopropylinden-1-yl)dimethylsilane,
- bis(4-R-2-phenylinden-1-yl)dimethylsilane,
- (4-R-2-methylinden-1-yl)(4-fluoro-2-methylinden-1-yl)dimethylsilane,
- (4-R-2-methylinden-1-yl)(2-methylinden-1-yl)dimethylsilane,
- (4-R-2-methylinden-1-yl)(2-isopropylinden-1-yl)dimethylsilane,
- (4-R-2-methylinden-1-yl)(inden-1-yl)dimethylsilane,
- (4-R-2-methylinden-1-yl)(inden-2-yl)dimethylsilane,
- (4-R-2-methylinden-1-yl)(2,4,6-trimethylinden-1-yl)dimethylsilane,
- (4-R-2-methylinden-1-yl)(4-phenyl-2-methylinden-1-yl)dimethylsilane,
- (4-R-2-methylinden-1-yl)(4-naphthyl-2-methylinden-1-yl)dimethylsilane,
- (4-R-2-methylinden-1-yl)[4-(2,5-dimethylphenyl)-2-methylinden-1-yl]dimethylsilane,
- (4-R-2-methylinden-1-yl)[4-(3,5-dimethylphenyl)-2-methylinden-1-yl]dimethylsilane,
- (4-R-2-methylinden-1-yl)[4-(3,5-diisopropylphenyl)-2-methylinden-1-yl]dimethylsilane,
- (4-R-2-methylinden-1-yl)[4-(3,5-di-tert-butylphenyl)-2-methylinden-1-yl]dimethylsilane,
- (4-R-2-methylinden-1-yl)[4-(2-thienyl)-2-methylinden-1-yl]dimethylsilane,
- (4-R-2-methylinden-1-yl)[4-(4-pyridyl)-2-methylinden-1-yl]dimethylsilane,
- (4-R-2-methylinden-1-yl)(4-tert-butyl-2-methylinden-1-yl)dimethylsilane,
- (4-R-2-methylinden-1-yl)(4-cyclohexyl-2-methylinden-1-yl)dimethylsilane,
- (4-R-2-methylinden-1-yl)(4-isopropyl-2-methylinden-1-yl)dimethylsilane,
- (4-R-2-methylinden-1-yl)(4-trimethysilyl-2-methylinden-1-yl)dimethylsilane,
- (4-R-2-methylinden-1-yl)(4-trimethylgermyl-2-methylinden-1-yl)dimethylsilane,
- (4-R-2-methylinden-1-yl)(4-methylthio-2-methylinden-1-yl)dimethylsilane,
- (4-R-2-methylinden-1-yl)(4-diphenylphosphino-2-methylinden-1-yl)dimethylsilane,
- (4-R-2-methylinden-1-yl)(4-trifluoromethyl-2-methylinden-1-yl)dimethylsilane,
- (4-R-2-methylinden-1-yl)(cyclopentadienyl)dimethylsilane,
- (4-R-2-methylinden-1-yl)(3-methylcyclopentadien-1-yl)dimethylsilane,
- (4-R-2-methylinden-1-yl)(3-tert-butylcyclopentadien-1-yl)dimethylsilane,
- (4-R-2-methylinden-1-yl)(3-trimethylsilylcyclopentadien-1-yl)dimethylsilane,
- (4-R-2-methylinden-1-yl)(3-phenylcyclopentadien-1-yl)dimethylsilane,
- (4-R-2-methylinden-1-yl) [3-(2-thienyl)cyclopentadien-1-yl]dimethylsilane,
- (4-R-2-methylinden-1-yl)(3-diphenylphosphinocyclopentadien-1-yl)dimethylsilane,
- (4-R-2-methylinden-1-yl)(2,3,4,5-tetramethylcyclopentadien-1-yl)dimethylsilane,
- (4-R-2-methylinden-1-yl)(fluoren-9-yl)dimethylsilane,
- (4-R-2-methylinden-1-yl)(3,6-dimethylfluoren-9-yl)dimethylsilane,
- (4-R-2-methylinden-1-yl)(3,6-di-tert-butylfluoren-9-yl)dimethylsilane,
- (4-R-2-methylinden-1-yl)(2,7-di-fluoren-9-yl)dimethylsilane,
- (2-methylinden-1-yl)(2,7-di-R-fluoren-9-yl)dimethylsilane,
- (2-methyl-4-phenylinden-1-yl)(2,7-di-R-fluoren-9-yl)dimethylsilane,
- (2,4-dimethylinden-1-yl)(2,7-di-R-fluoren-9-yl)dimethylsilane,
- (2-methyl-4-trimethylsilylinden-1-yl)(2,7-di-R-fluoren-9-yl)dimethylsilane,
- (2-methyl-4-tert-butylinden-1-yl)(2,7-di-R-fluoren-9-yl)dimethylsilane,
- (2-methyl-4-methoxyinden-1-yl)(2,7-di-R-fluoren-9-yl)dimethylsilane,
- (2-methyl-4-dimethylaminoinden-1-yl)(2,7-di-R-fluoren-9-yl)dimethylsilane,
- (2-methyl-4-trifluoromethylinden-1-yl)(2,7-di-R-fluoren-9-yl)dimethylsilane,
- (cyclopentadienyl)(2,7-di-R-fluoren-9-yl)dimethylsilane,
- (3-methylcyclopentadien-1-yl)(2,7-di-R-fluoren-9-yl)dimethylsilane,
- (3-tert-butylcyclopentadien-1-yl)(2,7-di-R-fluoren-9-yl)dimethylsilane,
- (3-phenylcyclopentadien-1-yl)(2,7-di-R-fluoren-9-yl)dimethylsilane,
- (3-trimethylsilylcyclopentadien-1-yl)(2,7-di-R-fluoren-9-yl)dimethylsilane,
- (3,4-dimethylcyclopentadien-1-yl)(2,7-di-R-fluoren-9-yl)dimethylsilane,
- [3-(2-thienyl)cyclopentadien-1-yl](2,7-di-R-fluoren-9-yl)dimethylsilane,
- (fluoren-9-yl)(2,7-di-R-fluoren-9-yl)dimethylsilane,
- (3,6-dimethylfluoren-9-yl)(2,7-di-R-fluoren-9-yl)dimethylsilane,
- (3,6-ditertbutylfluoren-9-yl)(2,7-di-R-fluoren-9-yl)dimethylsilane,
- (3,6-diphenylfluoren-9-yl)(2,7-di-R-fluoren-9-yl)dimethylsilane,
- bis(4-R-2-methyl-5,6,7,8-tetrahydrocyclopenta[b]naphth-1-yl)dimethylsilane,
- bis(5-R-2-methyl-6,7,8,9-tetrahydrocyclopenta[a]naphth-3-yl)dimethylsilane,
- bis(4-R-2-methylcyclopenta[b]naphth-1-yl)dimethylsilane,
- bis(7-R-2,4-dimethylcyclopenta[b]naphth-1-yl)dimethylsilane,
- bis(8-R-6-methylindeno[5,6-d][1,3]dioxol-5-yl)dimethylsilane,
- bis(4-R-2,3,6-trimethylindeno[5,6-b]thien-7-yl)dimethylsilane,
- bis(2-R-4,6-dimethylindeno[5,6-b]thien-7-yl)dimethylsilane,
- bis(4-R-1,2,3,6-tetramethylcyclopenta[f]indol-7-yl)dimethylsilane,
- bis(4-R-1-phenyl-2,3,6-trimethylcyclopenta[/]indol-7-yl)dimethylsilane,
- bis(5-R-7-methylcyclopenta[g]quinol-8-yl)dimethylsilane,
- bis(2-R-5,7-dimethylcyclopenta[g]quinol-8-yl)dimethylsilane,
- (cyclopentadienyl)(4-R-2-methyl-5,6,7,8-tetrahydrocyclopenta[b]naphth-1-yl)dimethylsilane,
- (cyclopentadienyl)(5-R-2-methyl-6,7,8,9-tetrahydrocyclopenta[a]naphth-3-yl)dimethylsilane,
- (cyclopentadienyl)(4-R-2-methylcyclopenta[b]naphth-1-yl)dimethylsilane,
- (cyclopentadienyl)(7-R-2,4-dimethylcyclopenta[b]naphth-1-yl)dimethylsilane,
- (cyclopentadienyl)(8-R-6-methylindeno[5,6-d][1,3]dioxol-5-yl)dimethylsilane,
- (cyclopentadienyl)(4-R-2,3,6-trimethylindeno[5,6-b]thien-7-yl)dimethylsilane,
- (cyclopentadienyl)(2-R-4,6-dimethylindeno[5,6-b]thien-7-yl)dimethylsilane,
- (cyclopentadienyl)(4-R-1,2,3,6-tetramethylcyclopenta[/]indol-7-yl)dimethylsilane,
- (cyclopentadienyl)(4-R-1-phenyl-2,3,6-trimethylcyclopenta[f]indol-7-yl)dimethylsilane,
- (cyclopentadienyl)(5-R-7-methylcyclopenta[g]quinol-8-yl)dimethylsilane,
- (cyclopentadienyl)(2-R-5,7-dimethylcyclopenta[g]quinol-8-yl)dimethylsilane,
- (inden-1-yl)(4-R-2-methyl-5,6,7,8-tetrahydrocyclopenta[b]naphth-1-yl)dimethylsilane,
- (inden-1-yl)(5-R-2-methyl-6,7,8,9-tetrahydrocyclopenta[a]naphth-3-yl)dimethylsilane,
- (inden-1-yl)(4-R-2-methylcyclopenta[b]naphth-1-yl)dimethylsilane,
- (inden-1-yl)(7-R-2,4-dimethylcyclopenta[b]naphth-1-yl)dimethylsilane,
- (inden-1-yl)(8-R-6-methylindeno[5,6-d][1,3]dioxol-5-yl)dimethylsilane,
- (inden-1-yl)(4-R-2,3,6-trimethylindeno[5,6-b]thien-7-yl)dimethylsilane,
- (inden-1-yl)(2-R-4,6-dimethylindeno[5,6-b]thien-7-yl)dimethylsilane,
- (inden-1-yl)(4-R-1,2,3,6-tetramethylcyclopenta[f]indol-7-yl)dimethylsilane,
- (inden-1-yl)(4-R-1-phenyl-2,3,6-trimethylcyclopenta[f]indol-7-yl)dimethylsilane,
- (inden-1-yl)(5-R-7-methylcyclopenta[g]quinol-8-yl)dimethylsilane,
- (inden-1-yl)(2-R-5,7-dimethylcyclopenta[g]quinol-8-yl)dimethylsilane,
- (inden-2-yl)(4-R-2-methyl-5,6,7,8-tetrahydrocyclopenta[b]naphth-1-yl)dimethylsilane,
- (inden-2-yl)(5-R-2-methyl-6,7,8,9-tetrahydrocyclopenta[a]naphth-3-yl)dimethylsilane,
- (inden-2-yl)(4-R-2-methylcyclopenta[b]naphth-1-yl)dimethylsilane,
- (inden-2-yl)(7-R-2,4-dimethylcyclopenta[b]naphth-1-yl)dimethylsilane,
- (inden-2-yl)(8-R-6-methylindeno[5,6-d][1,3]dioxol-5-yl)dimethylsilane,
- (inden-2-yl)(4-R-2,3,6-trimethylindeno[5,6-b]thien-7-yl)dimethylsilane,
- (inden-2-yl)(2-R-4,6-dimethylindeno[5,6-b]thien-7-yl)dimethylsilane,
- (inden-2-yl)(4-R-1,2,3,6-tetramethylcyclopenta[/]indol-7-yl)dimethylsilane,
- (inden-2-yl)(4-R-1-phenyl-2,3,6-trimethylcyclopenta[f]indol-7-yl)dimethylsilane,
- (inden-2-yl)(5-R-7-methylcyclopenta[g]quinol-8-yl)dimethylsilane,
- (inden-2-yl)(2-R-5,7-dimethylcyclopenta[g]quinol-8-yl)dimethylsilane,
- (4-R-2-methylinden-1-yl)(4-R-2-methyl-5,6,7,8-tetrahydrocyclopenta[b]naphth-1-yl)dimethylsilane,
- (4-R-2-methylinden-1-yl)(5-R-2-methyl-6,7,8,9-tetrahydrocyclopenta[a]naphth-3-yl)dimethylsilane,
- (4-R-2-methylinden-1-yl)(4-R-2-methylcyclopenta[b]naphth-1-yl)dimethylsilane,
- (4-R-2-methylinden-1-yl)(7-R-2,4-dimethylcyclopenta[b]naphth-1-yl)dimethylsilane,
- (4-R-2-methylinden-1-yl)(8-R-6-methylindeno[5,6-d][1,3]dioxol-5-yl)dimethylsilane,
- (4-R-2-methylinden-1-yl)(4-R-2,3,6-trimethylindeno[5,6-b]thien-7-yl)dimethylsilane,
- (4-R-2-methylinden-1-yl)(2-R-4,6-dimethylindeno[5,6-b]thien-7-yl)dimethylsilane,
- (4-R-2-methylinden-1-yl)(4-R-1,2,3,6-tetramethylcyclopenta[f]indol-7-yl)dimethylsilane,
- (4-R-2-methylinden-1-yl)(4-R-1-phenyl-2,3,6-trimethylcyclopenta[/]indol-7-yl)dimethylsilane,
- (4-R-2-methylinden-1-yl)(5-R-7-methylcyclopenta[g]quinol-8-yl)dimethylsilane,
- (4-R-2-methylinden-1-yl)(2-R-5,7-dimethylcyclopenta[g]quinol-8-yl)dimethylsilane,
- (fluoren-9-yl)(4-R-2-methyl-5,6,7,8-tetrahydrocyclopenta[b]naphth-1-yl)dimethylsilane,
- (fluoren-9-yl)(5-R-2-methyl-6,7,8,9-tetrahydrocyclopenta[a]naphth-3-yl)dimethylsilane,
- (fluoren-9-yl)(4-R-2-methylcyclopenta[b]naphth-1-yl)dimethylsilane,
- (fluoren-9-yl)(7-R-2,4-dimethylcyclopenta[b]naphth-1-yl)dimethylsilane,
- (fluoren-9-yl)(8-R-6-methylindeno[5,6-d][1,3]dioxol-5-yl)dimethylsilane,
- (fluoren-9-yl)(4-R-2,3,6-trimethylindeno[5,6-b]thien-7-yl)dimethylsilane,
- (fluoren-9-yl)(2-R-4,6-dimethylindeno[5,6-b]thien-7-yl)dimethylsilane,
- (fluoren-9-yl)(4-R-1,2,3,6-tetramethylcyclopenta[/]indol-7-yl)dimethylsilane,
- (fluoren-9-yl)(4-R-1-phenyl-2,3,6-trimethylcyclopenta[f]indol-7-yl)dimethylsilane,
- (fluoren-9-yl)(5-R-7-methylcyclopenta[g]quinol-8-yl)dimethylsilane,
- (fluoren-9-yl)(2-R-5,7-dimethylcyclopenta[g]quinol-8-yl)dimethylsilane,
- 2,2′-bis(4-R-3-dimethylamino-1,3-benzothiaborollideyl)dimethylsilane,
- bis(4-R-3a,7a-azaborinden-1-yl)dimethylsilane,
- 3,3′-bis(7-R-2-dimethylamino-1,2-benzothiaborollide)dimethylsilane,
- 5,5′-bis(3-R-2-dimethylamino-1,2-thiaborollide)dimethylsilane,
- 1,2′-(cyclopentadienyl)(4-R-3-dimethylamino-1,3-benzothiaborollide) dimethylsilane,
- (cyclopentadienyl)(4-R-3a,7a-azaborinden-1-yl)dimethylsilane,
- 1,3′-(cyclopentadienyl)(7-R-2-dimethylamino-1,2-benzothiaborollide) dimethylsilane,
- 1,5′-(cyclopentadienyl)(3-R-2-dimethylamino-1,2-thiaborollide)dimethylsilane,
- 1,2′-(indenyl)(4-R-3-dimethylamino-1,3-benzothiaborollide)dimethylsilane,
- (inden-1-yl)(4-R-3a,7a-azaborinden-1-yl)dimethylsilane,
- 1,3′-(indenyl)(7-R-2-dimethylamino-1,2-benzothiaborollide)dimethylsilane,
- 1,5′-(indenyl)(3-R-2-dimethylamino-1,2-thiaborollide)dimethylsilane,
- 2,2′-(indenyl)(4-R-3-dimethylamino-1,3-benzothiaborollide)dimethylsilane,
- (inden-2-yl)(4-R-3a,7a-azaborinden-1-yl)dimethylsilane,
- 2,3′-(indenyl)(7-R-2-dimethylamino-1,2-benzothiaborollide)dimethylsilane,
- 2,5′-(indenyl)(3-R-2-dimethylamino-1,2-thiaborollide)dimethylsilane,
- 9,2′-(fluorenyl)(4-R-3-dimethylamino-1,3-benzothiaborollide)dimethylsilane,
- (fluoren-9-yl)(4-R-3a,7a-azaborinden-1-yl)dimethylsilane,
- 9,3′-(fluorenyl)(7-R-2-dimethylamino-1,2-benzothiaborollide)dimethylsilane,
- 9,5′-(fluorenyl)(3-R-2-dimethylamino-1,2-thiaborollide)dimethylsilane,
- bis(4-R-inden-1-yl)methane,
- bis(4-R-inden-2-yl)methane,
- (4-R-inden-1-yl)(4-R-inden-2-yl)methane,
- bis(4,6-di-R-2-methylinden-1-yl)methane,
- bis(4-R-2,6-dimethylinden-1-yl)methane,
- bis(4-R-2-methyl-6-isopropylinden-1-yl)methane,
- bis(4-R-2-methyl-6-fluoroinden-1-yl)methane,
- bis(4-R-2-methyl-6-methoxyinden-1-yl)methane,
- bis(4-R-2-methyl-6-dimethylaminoinden-1-yl)methane,
- bis(4-R-2-methyl-6-diphenylphosphinoinden-1-yl)methane,
- bis(4-R-2-methyl-6-methylsulfoinden-1-yl)methane,
- bis(4-R-2-methyl-6-trimethylsilylinden-1-yl)methane,
- bis(4-R-2-methyl-6-phenylinden-1-yl)methane,
- bis(4-R-2-methyl-6-naphthylinden-1-yl)methane,
- bis(4-R-2-methyl-6-N-indolylinden-1-yl)methane,
- bis(4-R-2-methyl-6-trifluoromethylinden-1-yl)methane,
- bis[4-R-2-methyl-6-(2-thienyl)inden-1-yl]methane,
- bis[4-R-2-methyl-6-(4-pyridyl)inden-1-yl]methane,
- bis(4-R-2-ethylinden-1-yl)methane,
- bis(4-R-2-isopropylinden-1-yl)methane,
- bis(4-R-2-phenylinden-1-yl)methane,
- (4-R-2-methylinden-1-yl)(4-fluoro-2-methylinden-1-yl)methane,
- (4-R-2-methylinden-1-yl)(2-methylinden-1-yl)methane,
- (4-R-2-methylinden-1-yl)(2-isopropylinden-1-yl)methane,
- (4-R-2-methylinden-1-yl)(inden-1-yl)methane,
- (4-R-2-methylinden-1-yl)(inden-2-yl)methane,
- (4-R-2-methylinden-1-yl)(2,4,6-trimethylinden-1-yl)methane,
- (4-R-2-methylinden-1-yl)(4-phenyl-2-methylinden-1-yl)methane,
- (4-R-2-methylinden-1-yl)(4-naphthyl-2-methylinden-1-yl)methane,
- (4-R-2-methylinden-1-yl)[4-(2,5-dimethylphenyl)-2-methylinden-1-yl]methane,
- (4-R-2-methylinden-1-yl)[4-(3,5-dimethylphenyl)-2-methylinden-1-yl]methane,
- (4-R-2-methylinden-1-yl)[4-(3,5-diisopropylphenyl)-2-methylinden-1-yl]methane,
- (4-R-2-methylinden-1-yl)[4-(3,5-di-tert-butylphenyl)-2-methylinden-1-yl]methane,
- (4-R-2-methylinden-1-yl)[4-(2-thienyl)-2-methylinden-1-yl]methane,
- (4-R-2-methylinden-1-yl) [4-(4-pyridyl)-2-methylinden-1-yl]methane,
- (4-R-2-methylinden-1-yl)(4-tert-butyl-2-methylinden-1-yl)methane,
- (4-R-2-methylinden-1-yl)(4-cyclohexyl-2-methylinden-1-yl)methane,
- (4-R-2-methylinden-1-yl)(4-isopropyl-2-methylinden-1-yl)methane,
- (4-R-2-methylinden-1-yl)(4-trimethysilyl-2-methylinden-1-yl)methane,
- (4-R-2-methylinden-1-yl)(4-trimethylgermyl-2-methylinden-1-yl)methane,
- (4-R-2-methylinden-1-yl)(4-methylthio-2-methylinden-1-yl)methane,
- (4-R-2-methylinden-1-yl)(4-diphenylphosphino-2-methylinden-1-yl)methane,
- (4-R-2-methylinden-1-yl)(4-trifluoromethyl-2-methylinden-1-yl)methane,
- (4-R-2-methylinden-1-yl)(cyclopentadienyl)methane,
- (4-R-2-methylinden-1-yl)(3-methylcyclopentadien-1-yl)methane,
- (4-R-2-methylinden-1-yl)(3-tert-butylcyclopentadien-1-yl)methane,
- (4-R-2-methylinden-1-yl)(3-trimethylsilylcyclopentadien-1-yl)methane,
- (4-R-2-methylinden-1-yl)(3-phenylcyclopentadien-1-yl)methane,
- (4-R-2-methylinden-1-yl)[3-(2-thienyl)cyclopentadien-1-yl]methane,
- (4-R-2-methylinden-1-yl)(3-diphenylphosphinocyclopentadien-1-yl)methane,
- (4-R-2-methylinden-1-yl)(2,3,4,5-tetramethylcyclopentadien-1-yl)methane,
- (4-R-2-methylinden-1-yl)(fluoren-9-yl)methane,
- (4-R-2-methylinden-1-yl)(3,6-dimethylfluoren-9-yl)methane,
- (4-R-2-methylinden-1-yl)(3,6-di-tert-butylfluoren-9-yl)methane,
- (4-R-2-methylinden-1-yl)(2,7-di-R-fluoren-9-yl)methane,
- (2-methylinden-1-yl)(2,7-di-R-fluoren-9-yl)methane,
- (2-methyl-4-phenylinden-1-yl)(2,7-di-R-fluoren-9-yl)methane,
- (2,4-dimethylinden-1-yl)(2,7-di-R-fluoren-9-yl)methane,
- (2-methyl-4-trimethylsilylinden-1-yl)(2,7-di-R-fluoren-9-yl)methane,
- (2-methyl-4-tert-butylinden-1-yl)(2,7-di-R-fluoren-9-yl)methane,
- (2-methyl-4-methoxyinden-1-yl)(2,7-di-R-fluoren-9-yl)methane,
- (2-methyl-4-dimethylaminoinden-1-yl)(2,7-di-R-fluoren-9-yl)methane,
- (2-methyl-4-trifluoromethylinden-1-yl)(2,7-di-R-fluoren-9-yl)methane,
- (cyclopentadienyl)(2,7-di-R-fluoren-9-yl)methane,
- (3-methylcyclopentadien-1-yl)(2,7-di-R-fluoren-9-yl)methane,
- (3-tert-butylcyclopentadien-1-yl)(2,7-di-R-fluoren-9-yl)methane,
- (3-phenylcyclopentadien-1-yl)(2,7-di-R-fluoren-9-yl)methane,
- (3-trimethylsilylcyclopentadien-1-yl)(2,7-di-R-fluoren-9-yl)methane,
- (3,4-dimethylcyclopentadien-1-yl)(2,7-di-R-fluoren-9-yl)methane,
- [3-(2-thienyl)cyclopentadien-1-yl] (2,7-di-R-fluoren-9-yl)methane,
- (fluoren-9-yl)(2,7-di-R-fluoren-9-yl)methane,
- (3,6-dimethylfluoren-9-yl)(2,7-di-R-fluoren-9-yl)methane,
- (3,6-ditertbutylfluoren-9-yl)(2,7-di-R-fluoren-9-yl)methane,
- (3,6-diphenylfluoren-9-yl)(2,7-di-R-fluoren-9-yl)methane,
- bis(4-R-2-methyl-5,6,7,8-tetrahydrocyclopenta[b]naphth-1-yl)methane,
- bis(5-R-2-methyl-6,7,8,9-tetrahydrocyclopenta[a]naphth-3-yl)methane,
- bis(4-R-2-methylcyclopenta[b]naphth-1-yl)methane,
- bis(7-R-2,4-dimethylcyclopenta[b]naphth-1-yl)methane,
- bis(8-R-6-methylindeno[5,6-d][1,3]dioxol-5-yl)methane,
- bis(4-R-2,3,6-trimethylindeno[5,6-b]thien-7-yl)methane,
- bis(2-R-4,6-dimethylindeno[5,6-b]thien-7-yl)methane,
- bis(4-R-1,2,3,6-tetramethylcyclopenta[/]indol-7-yl)methane,
- bis(4-R-1-phenyl-2,3,6-trimethylcyclopenta[/]indol-7-yl)methane,
- bis(5-R-7-methylcyclopenta[g]quinol-8-yl)methane,
- bis(2-R-5,7-dimethylcyclopenta[g]quinol-8-yl)methane,
- (cyclopentadienyl)(4-R-2-methyl-5,6,7,8-tetrahydrocyclopenta[b]naphth-1-yl)methane,
- (cyclopentadienyl)(5-R-2-methyl-6,7,8,9-tetrahydrocyclopenta[a]naphth-3-yl)methane,
- (cyclopentadienyl)(4-R-2-methylcyclopenta[b]naphth-1-yl)methane,
- (cyclopentadienyl)(7-R-2,4-dimethylcyclopenta[b]naphth-1-yl)methane,
- (cyclopentadienyl)(8-R-6-methylindeno[5,6-d][1,3]dioxol-5-yl)methane,
- (cyclopentadienyl)(4-R-2,3,6-trimethylindeno[5,6-b]thien-7-yl)methane,
- (cyclopentadienyl)(2-R-4,6-dimethylindeno[5,6-b]thien-7-yl)methane,
- (cyclopentadienyl)(4-R-1,2,3,6-tetramethylcyclopenta[f])indol-7-yl)methane,
- (cyclopentadienyl)(4-R-1-phenyl-2,3,6-trimethylcyclopenta[f]indol-7-yl)methane,
- (cyclopentadienyl)(5-R-7-methylcyclopenta[g]quinol-8-yl)methane,
- (cyclopentadienyl)(2-R-5,7-dimethylcyclopenta[g]quinol-8-yl)methane,
- (inden-1-yl)(4-R-2-methyl-5,6,7,8-tetrahydrocyclopenta[b]naphth-1-yl)methane,
- (inden-1-yl)(5-R-2-methyl-6,7,8,9-tetrahydrocyclopenta[a]naphth-3-yl)methane,
- (inden-1-yl)(4-R-2-methylcyclopenta[b]naphth-1-yl)methane,
- (inden-1-yl)(7-R-2,4-dimethylcyclopenta[b]naphth-1-yl)methane,
- (inden-1-yl)(8-R-6-methylindeno[5,6-d][1,3]dioxol-5-yl)methane,
- (inden-1-yl)(4-R-2,3,6-trimethylindeno[5,6-b]thien-7-yl)methane,
- (inden-1-yl)(2-R-4,6-dimethylindeno[5,6-b]thien-7-yl)methane,
- (inden-1-yl)(4-R-1,2,3,6-tetramethylcyclopenta[f]indol-7-yl)methane,
- (inden-1-yl)(4-R-1-phenyl-2,3,6-trimethylcyclopenta[f]indol-7-yl)methane,
- (inden-2-yl)(4-R-cyclopenta[b]pyrid-7-yl)methane,
- (inden-1-yl)(5-R-7-methylcyclopenta[g]quinol-8-yl)methane,
- (inden-1-yl)(2-R-5,7-dimethylcyclopenta[g]quinol-8-yl)methane,
- (inden-2-yl)(4-R-2-methyl-5,6,7,8-tetrahydrocyclopenta[b]naphth-1-yl)methane,
- (inden-2-yl)(5-R-2-methyl-6,7,8,9-tetrahydrocyclopenta[a]naphth-3-yl)methane,
- (inden-2-yl)(4-R-2-methylcyclopenta[b]naphth-1-yl)methane,
- (inden-2-yl)(7-R-2,4-dimethylcyclopenta[b]naphth-1-yl)methane,
- (inden-2-yl)(8-R-6-methylindeno[5,6-d][1,3]dioxol-5-yl)methane,
- (inden-2-yl)(4-R-2,3,6-trimethylindeno[5,6-b]thien-7-yl)methane,
- (inden-2-yl)(2-R-4,6-dimethylindeno[5,6-b]thien-7-yl)methane,
- (inden-2-yl)(4-R-1,2,3,6-tetramethylcyclopenta[f]indol-7-yl)methane,
- (inden-2-yl)(4-R-1-phenyl-2,3,6-trimethylcyclopenta[/]indol-7-yl)methane,
- (inden-2-yl)(5-R-7-methylcyclopenta[g]quinol-8-yl)methane,
- (inden-2-yl)(2-R-5,7-dimethylcyclopenta[g]quinol-8-yl)methane,
- (4-R-2-methylinden-1-yl)(4-R-2-methyl-5,6,7,8-tetrahydrocyclopenta[b]naphth-1-yl)methane,
- (4-R-2-methylinden-1-yl)(5-R-2-methyl-6,7,8,9-tetrahydrocyclopenta[a]naphth-3-yl)methane,
- (4-R-2-methylinden-1-yl)(4-R-2-methylcyclopenta[b]naphth-1-yl)methane,
- (4-R-2-methylinden-1-yl)(7-R-2,4-dimethylcyclopenta[b]naphth-1-yl)methane,
- (4-R-2-methylinden-1-yl)(8-R-6-methylindeno[5,6-d][1,3]dioxol-5-yl)methane,
- (4-R-2-methylinden-1-yl)(4-R-2,3,6-trimethylindeno[5,6-b]thien-7-yl)methane,
- (4-R-2-methylinden-1-yl)(2-R-4,6-dimethylindeno[5,6-b]thien-7-yl)methane,
- (4-R-2-methylinden-1-yl)(4-R-1,2,3,6-tetramethylcyclopenta[/]indol-7-yl)methane,
- (4-R-2-methylinden-1-yl)(4-R-1-phenyl-2,3,6-trimethylcyclopenta[/]indol-7-yl)methane,
- (4-R-2-methylinden-1-yl)(5-R-7-methylcyclopenta[g]quinol-8-yl)methane,
- (4-R-2-methylinden-1-yl)(2-R-5,7-dimethylcyclopenta[g]quinol-8-yl)methane,
- (fluoren-9-yl)(4-R-2-methyl-5,6,7,8-tetrahydrocyclopenta[b]naphth-1-yl)methane,
- (fluoren-9-yl)(5-R-2-methyl-6,7,8,9-tetrahydrocyclopenta[a]naphth-3-yl)methane,
- (fluoren-9-yl)(4-R-2-methylcyclopenta[b]naphth-1-yl)methane,
- (fluoren-9-yl)(7-R-2,4-dimethylcyclopenta[b]naphth-1-yl)methane,
- (fluoren-9-yl)(8-R-6-methylindeno[5,6-d][1,3]dioxol-5-yl)methane,
- (fluoren-9-yl)(4-R-2,3,6-trimethylindeno[5,6-b]thien-7-yl)methane,
- (fluoren-9-yl)(2-R-4,6-dimethylindeno[5,6-b]thien-7-yl)methane,
- (fluoren-9-yl)(4-R-1,2,3,6-tetramethylcyclopenta[/]indol-7-yl)methane,
- (fluoren-9-yl)(4-R-1-phenyl-2,3,6-trimethylcyclopenta[f]indol-7-yl)methane,
- (fluoren-9-yl)(4-R-cyclopenta[b]pyrid-7-yl)methane,
- (fluoren-9-yl)(5-R-7-methylcyclopenta[g]quinol-8-yl)methane,
- (fluoren-9-yl)(2-R-5,7-dimethylcyclopenta[g]quinol-8-yl)methane,
- 2,2′-bis(4-R-3-dimethylamino-1,3-benzothiaborollide)methane,
- bis(4-R-3a,7a-azaborinden-1-yl)methane,
- 3,3′-bis(7-R-2-dimethylamino-1,2-benzothiaborollide)methane,
- 5,5′-bis(3-R-2-dimethylamino-1,2-thiaborollide)methane,
- 1,2′-(cyclopentadienyl)(4-R-3-dimethylamino-1,3-benzothiaborollide)methane,
- (cyclopentadienyl)(4-R-3a,7a-azaborinden-1-yl)methane,
- 1,3′-(cyclopentadienyl)(7-R-2-dimethylamino-1,2-benzothiaborollide)methane,
- 1,5′-(cyclopentadienyl)(3-R-2-dimethylamino-1,2-thiaborollide)methane,
- 1,2′-(indenyl)(4-R-3-dimethylamino-1,3-benzothiaborollide)methane,
- (inden-1-yl)(4-R-3a,7a-azaborinden-1-yl)methane,
- 1,3′-(indenyl)(7-R-2-dimethylamino-1,2-benzothiaborollide)methane,
- 1,5′-(indenyl)(3-R-2-dimethylamino-1,2-thiaborollide)methane,
- 2,2′-(indenyl)(4-R-3-dimethylamino-1,3-benzothiaborollide)methane,
- (inden-2-yl)(4-R-3a,7a-azaborinden-1-yl)methane,
- 2,3′-(indenyl)(7-R-2-dimethylamino-1,2-benzothiaborollide)methane,
- 2,5′-(indenyl)(3-R-2-dimethylamino-1,2-thiaborollide)methane,
- 9,2′-(fluorenyl)(4-R-3-dimethylamino-1,3-benzothiaborollide)methane,
- (fluoren-9-yl)(4-R-3a,7a-azaborinden-1-yl)methane,
- 9,3′-(fluorenyl)(7-R-2-dimethylamino-1,2-benzothiaborollide)methane,
- 9,5′-(fluorenyl)(3-R-2-dimethylamino-1,2-thiaborollide)methane,
- 2,2-bis(4-R-inden-1-yl)propane,
- 2,2-bis(4-R-inden-2-yl)propane,
- 2,2-(4-R-inden-1-yl)(4-R-inden-2-yl)propane,
- 2,2-bis(4,6-di-R-2-methylinden-1-yl)propane,
- 2,2-bis(4-R-2,6-dimethylinden-1-yl)propane,
- 2,2-bis(4-R-2-methyl-6-isopropylinden-1-yl)propane,
- 2,2-bis(4-R-2-methyl-6-fluoroinden-1-yl)propane,
- 2,2-bis(4-R-2-methyl-6-methoxyinden-1-yl)propane,
- 2,2-bis(4-R-2-methyl-6-dimethylaminoinden-1-yl)propane,
- 2,2-bis(4-R-2-methyl-6-diphenylphosphinoinden-1-yl)propane,
- 2,2-bis(4-R-2-methyl-6-methylsulfoinden-1-yl)propane,
- 2,2-bis(4-R-2-methyl-6-trimethylsilylinden-1-yl)propane,
- 2,2-bis(4-R-2-methyl-6-phenylinden-1-yl)propane,
- 2,2-bis(4-R-2-methyl-6-naphthylinden-1-yl)propane,
- 2,2-bis(4-R-2-methyl-6-N-indolylinden-1-yl)propane,
- 2,2-bis(4-R-2-methyl-6-trifluoromethylinden-1-yl)propane,
- 2,2-bis[4-R-2-methyl-6-(2-thienyl)inden-1-yl]propane,
- 2,2-bis[4-R-2-methyl-6-(4-pyridyl)inden-1-yl]propane,
- 2,2-bis(4-R-2-ethylinden-1-yl)propane,
- 2,2-bis(4-R-2-isopropylinden-1-yl)propane,
- 2,2-bis(4-R-2-phenylinden-1-yl)propane,
- 2-(4-R-2-methylinden-1-yl)-2-(4-fluoro-2-methylinden-1-yl)propane,
- 2-(4-R-2-methylinden-1-yl)-2-(2-methylinden-1-yl)propane,
- 2-(4-R-2-methylinden-1-yl)-2-(2-isopropylinden-1-yl)propane,
- 2-(4-R-2-methylinden-1-yl)-2-(inden-1-yl)propane,
- 2-(4-R-2-methylinden-1-yl)-2-(inden-2-yl)propane,
- 2-(4-R-2-methylinden-1-yl)-2-(2,4,6-trimethylinden-1-yl)propane,
- 2-(4-R-2-methylinden-1-yl)-2-(4-phenyl-2-methylinden-1-yl)propane,
- 2-(4-R-2-methylinden-1-yl)-2-(4-naphthyl-2-methylinden-1-yl)propane,
- 2-(4-R-2-methylinden-1-yl)-2-[4-(2,5-dimethylphenyl)-2-methylinden-1-yl]propane,
- 2-(4-R-2-methylinden-1-yl)-2-[4-(3,5-dimethylphenyl)-2-methylinden-1-yl]propane,
- 2-(4-R-2-methylinden-1-yl)-2-[4-(3,5-diisopropylphenyl)-2-methylinden-1-yl]propane,
- 2-(4-R-2-methylinden-1-yl)-2-[4-(3,5-di-tert-butylphenyl)-2-methylinden-1-yl]propane,
- 2-(4-R-2-methylinden-1-yl)-2-[4-(2-thienyl)-2-methylinden-1-yl]propane,
- 2-(4-R-2-methylinden-1-yl)-2-[4-(4-pyridyl)-2-methylinden-1-yl]propane,
- 2-(4-R-2-methylinden-1-yl)-2-(4-tert-butyl-2-methylinden-1-yl)propane,
- 2-(4-R-2-methylinden-1-yl)-2-(4-cyclohexyl-2-methylinden-1-yl)propane,
- 2-(4-R-2-methylinden-1-yl)-2-(4-isopropyl-2-methylinden-1-yl)propane,
- 2-(4-R-2-methylinden-1-yl)-2-(4-trimethysilyl-2-methylinden-1-yl)propane,
- 2-(4-R-2-methylinden-1-yl)-2-(4-trimethylgermyl-2-methylinden-1-yl)propane,
- 2-(4-R-2-methylinden-1-yl)-2-(4-methylthio-2-methylinden-1-yl)propane,
- 2-(4-R-2-methylinden-1-yl)-2-(4-diphenylphosphino-2-methylinden-1-yl)propane,
- 2-(4-R-2-methylinden-1-yl)-2-(4-trifluoromethyl-2-methylinden-1-yl)propane,
- 2-(4-R-2-methylinden-1-yl)-2-(cyclopentadienyl)propane,
- 2-(4-R-2-methylinden-1-yl)-2-(3-methylcyclopentadien-1-yl)propane,
- 2-(4-R-2-methylinden-1-yl)-2-(3-tert-butylcyclopentadien-1-yl)propane,
- 2-(4-R-2-methylinden-1-yl)-2-(3-trimethylsilylcyclopentadien-1-yl)propane,
- 2-(4-R-2-methylinden-1-yl)-2-(3-phenylcyclopentadien-1-yl)propane,
- 2-(4-R-2-methylinden-1-yl)-2-[3-(2-thienyl)cyclopentadien-1-yl]propane,
- 2-(4-R-2-methylinden-1-yl)-2-(3-diphenylphosphinocyclopentadien-1-yl)propane,
- 2-(4-R-2-methylinden-1-yl)-2-(2,3,4,5-tetramethylcyclopentadien-1-yl)propane,
- 2-(4-R-2-methylinden-1-yl)-2-(fluoren-9-yl)propane,
- 2-(4-R-2-methylinden-1-yl)-2-(3,6-dimethylfluoren-9-yl)propane,
- 2-(4-R-2-methylinden-1-yl)-2-(3,6-di-tert-butylfluoren-9-yl)propane,
- 2-(4-R-2-methylinden-1-yl)-2-(2,7-di-R-fluoren-9-yl)propane,
- 2-(2-methylinden-1-yl)-2-(2,7-di-R-fluoren-9-yl)propane,
- 2-(2-methyl-4-phenylinden-1-yl)-2-(2,7-di-R-fluoren-9-yl)propane,
- 2-(2,4-dimethylinden-1-yl)-2-(2,7-di-R-fluoren-9-yl)propane,
- 2-(2-methyl-4-trimethylsilylinden-1-yl)-2-(2,7-di-R-fluoren-9-yl)propane,
- 2-(2-methyl-4-tert-butylinden-1-yl)-2-(2,7-di-R-fluoren-9-yl)propane,
- 2-(2-methyl-4-methoxyinden-1-yl)-2-(2,7-di-R-fluoren-9-yl)propane,
- 2-(2-methyl-4-dimethylaminoinden-1-yl)-2-(2,7-di-R-fluoren-9-yl)propane,
- 2-(2-methyl-4-trifluoromethylinden-1-yl)-2-(2,7-di-R-fluoren-9-yl)propane,
- 2-(cyclopentadienyl)-2-(2,7-di-R-fluoren-9-yl)propane,
- 2-(3-methylcyclopentadien-1-yl)-2-(2,7-di-R-fluoren-9-yl)propane,
- 2-(3-tert-butylcyclopentadien-1-yl)-2-(2,7-di-R-fluoren-9-yl)propane,
- 2-(3-phenylcyclopentadien-1-yl)-2-(2,7-di-R-fluoren-9-yl)propane,
- 2-(3-trimethylsilylcyclopentadien-1-yl)-2-(2,7-di-R-fluoren-9-yl)propane,
- 2-(3,4-dimethylcyclopentadien-1-yl)-2-(2,7-di-R-fluoren-9-yl)propane,
- 2-[3-(2-thienyl)cyclopentadien-1-yl]-2-(2,7-di-R-fluoren-9-yl)propane,
- 2-(fluoren-9-yl)-2-(2,7-di-R-fluoren-9-yl)propane,
- 2-(3,6-dimethylfluoren-9-yl)-2-(2,7-di-R-fluoren-9-yl)propane,
- 2-(3,6-ditertbutylfluoren-9-yl)-2-(2,7-di-R-fluoren-9-yl)propane,
- 2-(3,6-diphenylfluoren-9-yl)-2-(2,7-di-R-fluoren-9-yl)propane,
- 2,2-bis(4-R-2-methyl-5,6,7,8-tetrahydrocyclopenta[b]naphth-1-yl)propane,
- 2,2-bis(5-R-2-methyl-6,7,8,9-tetrahydrocyclopenta[a]naphth-3-yl)propane,
- 2,2-bis(4-R-2-methylcyclopenta[b]naphth-1-yl)propane,
- 2,2-bis(7-R-2,4-dimethylcyclopenta[b]naphth-1-yl)propane,
- 2,2-bis(8-R-6-methylindeno[5,6-d][1,3]dioxol-5-yl)propane,
- 2,2-bis(4-R-2,3,6-trimethylindeno[5,6-b]thien-7-yl)propane,
- 2,2-bis(2-R-4,6-dimethylindeno[5,6-b]thien-7-yl)propane,
- 2,2-bis(4-R-1,2,3,6-tetramethylcyclopenta[/]indol-7-yl)propane,
- 2,2-bis(4-R-1-phenyl-2,3,6-trimethylcyclopenta[/]indol-7-yl)propane,
- 2,2-bis(5-R-7-methylcyclopenta[g]quinol-8-yl)propane,
- 2,2-bis(2-R-5,7-dimethylcyclopenta[g]quinol-8-yl)propane,
- 2-(cyclopentadienyl)-2-(4-R-2-methyl-5,6,7,8-tetrahydrocyclopenta[b]naphth-1-yl)propane,
- 2-(cyclopentadienyl)-2-(5-R-2-methyl-6,7,8,9-tetrahydrocyclopenta[a]naphth-3-yl)propane,
- 2-(cyclopentadienyl)-2-(4-R-2-methylcyclopenta[b]naphth-1-yl)propane,
- 2-(cyclopentadienyl)-2-(7-R-2,4-dimethylcyclopenta[b]naphth-1-yl)propane,
- 2-(cyclopentadienyl)-2-(8-R-6-methylindeno[5,6-d][1,3]dioxol-5-yl)propane,
- 2-(cyclopentadienyl)-2-(4-R-2,3,6-trimethylindeno[5,6-b]thien-7-yl)propane,
- 2-(cyclopentadienyl)-2-(2-R-4,6-dimethylindeno[5,6-b]thien-7-yl)propane,
- 2-(cyclopentadienyl)-2-(4-R-1,2,3,6-tetramethylcyclopenta[/]indol-7-yl)propane,
- 2-(cyclopentadienyl)-2-(4-R-1-phenyl-2,3,6-trimethylcyclopenta[f]indol-7-yl)propane,
- 2-(cyclopentadienyl)-2-(4-R-cyclopenta[b]pyrid-7-yl)propane,
- 2-(cyclopentadienyl)-2-(5-R-7-methylcyclopenta[g]quinol-8-yl)propane,
- 2-(cyclopentadienyl)-2-(2-R-5,7-dimethylcyclopenta[g]quinol-8-yl)propane,
- 2-(inden-1-yl)-2-(4-R-2-methyl-5,6,7,8-tetrahydrocyclopenta[b]naphth-1-yl)propane,
- 2-(inden-1-yl)-2-(5-R-2-methyl-6,7,8,9-tetrahydrocyclopenta[a]naphth-3-yl)propane,
- 2-(inden-1-yl)-2-(4-R-2-methylcyclopenta[b]naphth-1-yl)propane,
- 2-(inden-1-yl)-2-(7-R-2,4-dimethylcyclopenta[b]naphth-1-yl)propane,
- 2-(inden-1-yl)-2-(8-R-6-methylindeno[5,6-d][1,3]dioxol-5-yl)propane,
- 2-(inden-1-yl)-2-(4-R-2,3,6-trimethylindeno[5,6-b]thien-7-yl)propane,
- 2-(inden-1-yl)-2-(2-R-4,6-dimethylindeno[5,6-b]thien-7-yl)propane,
- 2-(inden-1-yl)-2-(4-R-1,2,3,6-tetramethylcyclopenta[/]indol-7-yl)propane,
- 2-(inden-1-yl)-2-(4-R-1-phenyl-2,3,6-trimethylcyclopenta[/]indol-7-yl)propane,
- 2-(inden-1-yl)-2-(5-R-7-methylcyclopenta[g]quinol-8-yl)propane,
- 2-(inden-1-yl)-2-(2-R-5,7-dimethylcyclopenta[g]quinol-8-yl)propane,
- 2-(inden-2-yl)-2-(4-R-2-methyl-5,6,7,8-tetrahydrocyclopenta[b]naphth-1-yl)propane,
- 2-(inden-2-yl)-2-(5-R-2-methyl-6,7,8,9-tetrahydrocyclopenta[a]naphth-3-yl)propane,
- 2-(inden-2-yl)-2-(4-R-2-methylcyclopenta[b]naphth-1-yl)propane,
- 2-(inden-2-yl)-2-(7-R-2,4-dimethylcyclopenta[b]naphth-1-yl)propane,
- 2-(inden-2-yl)-2-(8-R-6-methylindeno[5,6-d][1,3]dioxol-5-yl)propane,
- 2-(inden-2-yl)-2-(4-R-2,3,6-trimethylindeno[5,6-b]thien-7-yl)propane,
- 2-(inden-2-yl)-2-(2-R-4,6-dimethylindeno[5,6-b]thien-7-yl)propane,
- 2-(inden-2-yl)-2-(4-R-1,2,3,6-tetramethylcyclopenta[/]indol-7-yl)propane,
- 2-(inden-2-yl)-2-(4-R-1-phenyl-2,3,6-trimethylcyclopenta[f]indol-7-yl)propane,
- 2-(inden-2-yl)-2-(5-R-7-methylcyclopenta[g]quinol-8-yl)propane,
- 2-(inden-2-yl)-2-(2-R-5,7-dimethylcyclopenta[g]quinol-8-yl)propane,
- 2-(4-R-2-methylinden-1-yl)-2-(4-R-2-methyl-5,6,7,8-tetrahydrocyclopenta[b]naphth-1-yl)propane,
- 2-(4-R-2-methylinden-1-yl)-2-(5-R-2-methyl-6,7,8,9-tetrahydrocyclopenta[a]naphth-3-yl)propane,
- 2-(4-R-2-methylinden-1-yl)-2-(4-R-2-methylcyclopenta[b]naphth-1-yl)propane,
- 2-(4-R-2-methylinden-1-yl)-2-(7-R-2,4-dimethylcyclopenta[b]naphth-1-yl)propane,
- 2-(4-R-2-methylinden-1-yl)-2-(8-R-6-methylindeno[5,6-d][1,3]dioxol-5-yl)propane,
- 2-(4-R-2-methylinden-1-yl)-2-(4-R-2,3,6-trimethylindeno[5,6-b]thien-7-yl)propane,
- 2-(4-R-2-methylinden-1-yl)-2-(2-R-4,6-dimethylindeno[5,6-b]thien-7-yl)propane,
- 2-(4-R-2-methylinden-1-yl)-2-(4-R-1,2,3,6-tetramethylcyclopenta[/]indol-7-yl)propane,
- 2-(4-R-2-methylinden-1-yl)-2-(4-R-1-phenyl-2,3,6-trimethylcyclopenta[f]indol-7-yl)propane,
- 2-(4-R-2-methylinden-1-yl)-2-(4-R-cyclopenta[b]pyrid-7-yl)propane,
- 2-(4-R-2-methylinden-1-yl)-2-(5-R-7-methylcyclopenta[g]quinol-8-yl)propane,
- 2-(4-R-2-methylinden-1-yl)-2-(2-R-5,7-dimethylcyclopenta[g]quinol-8-yl)propane,
- 2-(fluoren-9-yl)-2-(4-R-2-methyl-5,6,7,8-tetrahydrocyclopenta[b]naphth-1-yl)propane,
- 2-(fluoren-9-yl)-2-(5-R-2-methyl-6,7,8,9-tetrahydrocyclopenta[a]naphth-3-yl)propane,
- 2-(fluoren-9-yl)-2-(4-R-2-methylcyclopenta[b]naphth-1-yl)propane,
- 2-(fluoren-9-yl)-2-(7-R-2,4-dimethylcyclopenta[b]naphth-1-yl)propane,
- 2-(fluoren-9-yl)-2-(8-R-6-methylindeno[5,6-d][1,3]dioxol-5-yl)propane,
- 2-(fluoren-9-yl)-2-(4-R-2,3,6-trimethylindeno[5,6-b]thien-7-yl)propane,
- 2-(fluoren-9-yl)-2-(2-R-4,6-dimethylindeno[5,6-b]thien-7-yl)propane,
- 2-(fluoren-9-yl)-2-(4-R-1,2,3,6-tetramethylcyclopenta[f]indol-7-yl)propane,
- 2-(fluoren-9-yl)-2-(4-R-1-phenyl-2,3,6-trimethylcyclopenta[f]indol-7-yl)propane,
- 2-(fluoren-9-yl)-2-(5-R-7-methylcyclopenta[g]quinol-8-yl)propane,
- 2-(fluoren-9-yl)-2-(2-R-5,7-dimethylcyclopenta[g]quinol-8-yl)propane,
- 1,2-bis(4-R-inden-1-yl)ethane,
- 1,2-bis(4-R-inden-2-yl)ethane,
- 1,2-(4-R-inden-1-yl)(4-R-inden-2-yl)ethane,
- 1,2-bis(4,6-di-R-2-methylinden-1-yl)ethane,
- 1,2-bis(4-R-2,6-dimethylinden-1-yl)ethane,
- 1,2-bis(4-R-2-methyl-6-isopropylinden-1-yl)ethane,
- 1,2-bis(4-R-2-methyl-6-fluoroinden-1-yl)ethane,
- 1,2-bis(4-R-2-methyl-6-methoxyinden-1-yl)ethane,
- 1,2-bis(4-R-2-methyl-6-dimethylaminoinden-1-yl)ethane,
- 1,2-bis(4-R-2-methyl-6-diphenylphosphinoinden-1-yl)ethane,
- 1,2-bis(4-R-2-methyl-6-methylsulfoinden-1-yl)ethane,
- 1,2-bis(4-R-2-methyl-6-trimethylsilylinden-1-yl)ethane,
- 1,2-bis(4-R-2-methyl-6-phenylinden-1-yl)ethane,
- 1,2-bis(4-R-2-methyl-6-naphthylinden-1-yl)ethane,
- 1,2-bis(4-R-2-methyl-6-N-indolylinden-1-yl)ethane,
- 1,2-bis(4-R-2-methyl-6-trifluoromethylinden-1-yl)ethane,
- 1,2-bis[4-R-2-methyl-6-(2-thienyl)inden-1-yl]ethane,
- 1,2-bis[4-R-2-methyl-6-(4-pyridyl)inden-1-yl]ethane,
- 1,2-bis(4-R-2-ethylinden-1-yl)ethane,
- 1,2-bis(4-R-2-isopropylinden-1-yl)ethane,
- 1,2-bis(4-R-2-phenylinden-1-yl)ethane,
- 1-(4-R-2-methylinden-1-yl)-2-(4-fluoro-2-methylinden-1-yl)ethane,
- 1-(4-R-2-methylinden-1-yl)-2-(2-methylinden-1-yl)ethane,
- 1-(4-R-2-methylinden-1-yl)-2-(2-isopropylinden-1-yl)ethane,
- 1-(4-R-2-methylinden-1-yl)-2-(inden-1-yl)ethane,
- 1-(4-R-2-methylinden-1-yl)-2-(inden-2-yl)ethane,
- 1-(4-R-2-methylinden-1-yl)-2-(2,4,6-trimethylinden-1-yl)ethane,
- 1-(4-R-2-methylinden-1-yl)-2-(4-phenyl-2-methylinden-1-yl)ethane,
- 1-(4-R-2-methylinden-1-yl)-2-(4-naphthyl-2-methylinden-1-yl)ethane,
- 1-(4-R-2-methylinden-1-yl)-2-[4-(2,5-dimethylphenyl)-2-methylinden-1-yl]ethane,
- 1-(4-R-2-methylinden-1-yl)-2-[4-(3,5-dimethylphenyl)-2-methylinden-1-yl]ethane,
- 1-(4-R-2-methylinden-1-yl)-2-[4-(3,5-diisopropylphenyl)-2-methylinden-1-yl]ethane,
- 1-(4-R-2-methylinden-1-yl)-2-[4-(3,5-di-tert-butylphenyl)-2-methylinden-1-yl]ethane,
- 1-(4-R-2-methylinden-1-yl)-2-[4-(2-thienyl)-2-methylinden-1-yl]ethane,
- 1-(4-R-2-methylinden-1-yl)-2-[4-(4-pyridyl)-2-methylinden-1-yl]ethane,
- 1-(4-R-2-methylinden-1-yl)-2-(4-tert-butyl-2-methylinden-1-yl)ethane,
- 1-(4-R-2-methylinden-1-yl)-2-(4-cyclohexyl-2-methylinden-1-yl)ethane,
- 1-(4-R-2-methylinden-1-yl)-2-(4-isopropyl-2-methylinden-1-yl)ethane,
- 1-(4-R-2-methylinden-1-yl)-2-(4-trimethysilyl-2-methylinden-1-yl)ethane,
- 1-(4-R-2-methylinden-1-yl)-2-(4-trimethylgermyl-2-methylinden-1-yl)ethane,
- 1-(4-R-2-methylinden-1-yl)-2-(4-methylthio-2-methylinden-1-yl)ethane,
- 1-(4-R-2-methylinden-1-yl)-2-(4-diphenylphosphino-2-methylinden-1-yl)ethane,
- 1-(4-R-2-methylinden-1-yl)-2-(4-trifluoromethyl-2-methylinden-1-yl)ethane,
- 1-(4-R-2-methylinden-1-yl)-2-(cyclopentadienyl)ethane,
- 1-(4-R-2-methylinden-1-yl)-2-(3-methylcyclopentadien-1-yl)ethane,
- 1-(4-R-2-methylinden-1-yl)-2-(3-tert-butylcyclopentadien-1-yl)ethane,
- 1-(4-R-2-methylinden-1-yl)-2-(3-trimethylsilylcyclopentadien-1-yl)ethane,
- 1-(4-R-2-methylinden-1-yl)-2-(3-phenylcyclopentadien-1-yl)ethane,
- 1-(4-R-2-methylinden-1-yl)-2-[3-(2-thienyl)cyclopentadien-1-yl]ethane,
- 1-(4-R-2-methylinden-1-yl)-2-(3-diphenylphosphinocyclopentadien-1-yl)ethane,
- 1-(4-R-2-methylinden-1-yl)-2-(2,3,4,5-tetramethylcyclopentadien-1-yl)ethane,
- 1-(4-R-2-methylinden-1-yl)-2-(fluoren-9-yl)ethane,
- 1-(4-R-2-methylinden-1-yl)-2-(3,6-dimethylfluoren-9-yl)ethane,
- 1-(4-R-2-methylinden-1-yl)-2-(3,6-di-tert-butylfluoren-9-yl)ethane,
- 1-(4-R-2-methylinden-1-yl)-2-(2,7-di-R-fluoren-9-yl)ethane,
- 1-(2-methylinden-1-yl)-2-(2,7-di-R-fluoren-9-yl)ethane,
- 1-(2-methyl-4-phenylinden-1-yl)-2-(2,7-di-R-fluoren-9-yl)ethane,
- 1-(2,4-dimethylinden-1-yl)-2-(2,7-di-R-fluoren-9-yl)ethane,
- 1-(2-methyl-4-trimethylsilylinden-1-yl)-2-(2,7-di-R-fluoren-9-yl)ethane,
- 1-(2-methyl-4-tert-butylinden-1-yl)-2-(2,7-di-R-fluoren-9-yl)ethane,
- 1-(2-methyl-4-methoxyinden-1-yl)-2-(2,7-di-R-fluoren-9-yl)ethane,
- 1-(2-methyl-4-dimethylaminoinden-1-yl)-2-(2,7-di-R-fluoren-9-yl)ethane,
- 1-(2-methyl-4-trifluoromethylinden-1-yl)-2-(2,7-di-R-fluoren-9-yl)ethane,
- 1-(cyclopentadienyl)-2-(2,7-di-R-fluoren-9-yl)ethane,
- 1-(3-methylcyclopentadien-1-yl)-2-(2,7-di-R-fluoren-9-yl)ethane,
- 1-(3-tert-butylcyclopentadien-1-yl)-2-(2,7-di-R-fluoren-9-yl)ethane,
- 1-(3-phenylcyclopentadien-1-yl)-2-(2,7-di-R-fluoren-9-yl)ethane,
- 1-(3-trimethylsilylcyclopentadien-1-yl)-2-(2,7-di-R-fluoren-9-yl)ethane,
- 1-(3,4-dimethylcyclopentadien-1-yl)-2-(2,7-di-R-fluoren-9-yl)ethane,
- 1-[3-(2-thienyl)cyclopentadien-1-yl]-2-(2,7-di-R-fluoren-9-yl)ethane,
- 1-(fluoren-9-yl)-2-(2,7-di-R-fluoren-9-yl)ethane,
- 1-(3,6-dimethylfluoren-9-yl)-2-(2,7-di-R-fluoren-9-yl)ethane,
- 1-(3,6-ditertbutylfluoren-9-yl)-2-(2,7-di-R-fluoren-9-yl)ethane,
- 1-(3,6-diphenylfluoren-9-yl)-2-(2,7-di-R-fluoren-9-yl)ethane,
- 1,2-bis(4-R-2-methyl-5,6,7,8-tetrahydrocyclopenta[b]naphth-1-yl)ethane,
- 1,2-bis(5-R-2-methyl-6,7,8,9-tetrahydrocyclopenta[a]naphth-3-yl)ethane,
- 1,2-bis(4-R-2-methylcyclopenta[b]naphth-1-yl)ethane,
- 1,2-bis(7-R-2,4-dimethylcyclopenta[b]naphth-1-yl)ethane,
- 1,2-bis(8-R-6-methylindeno[5,6-d][1,3]dioxol-5-yl)ethane,
- 1,2-bis(4-R-2,3,6-trimethylindeno[5,6-b]thien-7-yl)ethane,
- 1,2-bis(2-R-4,6-dimethylindeno[5,6-b]thien-7-yl)ethane,
- 1,2-bis(4-R-1,2,3,6-tetramethylcyclopenta[f]indol-7-yl)ethane,
- 1,2-bis(4-R-1-phenyl-2,3,6-trimethylcyclopenta[/]indol-7-yl)ethane,
- 1,2-bis(5-R-7-methylcyclopenta[g]quinol-8-yl)ethane,
- 1,2-bis(2-R-5,7-dimethylcyclopenta[g]quinol-8-yl)ethane,
- 1-(cyclopentadienyl)-2-(4-R-2-methyl-5,6,7,8-tetrahydrocyclopenta[b]naphth-1-yl)ethane,
- 1-(cyclopentadienyl)-2-(5-R-2-methyl-6,7,8,9-tetrahydrocyclopenta[a]naphth-3-yl)ethane,
- 1-(cyclopentadienyl)-2-(4-R-2-methylcyclopenta[b]naphth-1-yl)ethane,
- 1-(cyclopentadienyl)-2-(7-R-2,4-dimethylcyclopenta[b]naphth-1-yl)ethane,
- 1-(cyclopentadienyl)-2-(8-R-6-methylindeno[5,6-d][1,3]dioxol-5-yl)ethane,
- 1-(cyclopentadienyl)-2-(4-R-2,3,6-trimethylindeno[5,6-b]thien-7-yl)ethane,
- 1-(cyclopentadienyl)-2-(2-R-4,6-dimethylindeno[5,6-b]thien-7-yl)ethane,
- 1-(cyclopentadienyl)-2-(4-R-1,2,3,6-tetramethylcyclopenta[f]indol-7-yl)ethane,
- 1-(cyclopentadienyl)-2-(4-R-1-phenyl-2,3,6-trimethylcyclopenta[f]indol-7-yl)ethane,
- 1-(cyclopentadienyl)-2-(5-R-7-methylcyclopenta[g]quinol-8-yl)ethane,
- 1-(cyclopentadienyl)-2-(2-R-5,7-dimethylcyclopenta[g]quinol-8-yl)ethane,
- 1-(inden-1-yl)-2-(4-R-2-methyl-5,6,7,8-tetrahydrocyclopenta[b]naphth-1-yl)ethane,
- 1-(inden-1-yl)-2-(5-R-2-methyl-6,7,8,9-tetrahydrocyclopenta[a]naphth-3-yl)ethane,
- 1-(inden-1-yl)-2-(4-R-2-methylcyclopenta[b]naphth-1-yl)ethane,
- 1-(inden-1-yl)-2-(7-R-2,4-dimethylcyclopenta[b]naphth-1-yl)ethane,
- 1-(inden-1-yl)-2-(8-R-6-methylindeno[5,6-d][1,3]dioxol-5-yl)ethane,
- 1-(inden-1-yl)-2-(4-R-2,3,6-trimethylindeno[5,6-b]thien-7-yl)ethane,
- 1-(inden-1-yl)-2-(2-R-4,6-dimethylindeno[5,6-b]thien-7-yl)ethane,
- 1-(inden-1-yl)-2-(4-R-1,2,3,6-tetramethylcyclopenta[/]indol-7-yl)ethane,
- 1-(inden-1-yl)-2-(4-R-1-phenyl-2,3,6-trimethylcyclopenta[f]indol-7-yl)ethane,
- 1-(inden-1-yl)-2-(5-R-7-methylcyclopenta[g]quinol-8-yl)ethane,
- 1-(inden-1-yl)-2-(2-R-5,7-dimethylcyclopenta[g]quinol-8-yl)ethane,
- 1-(inden-2-yl)-2-(4-R-2-methyl-5,6,7,8-tetrahydrocyclopenta[b]naphth-1-yl)ethane,
- 1-(inden-2-yl)-2-(5-R-2-methyl-6,7,8,9-tetrahydrocyclopenta[a]naphth-3-yl)ethane,
- 1-(inden-2-yl)-2-(4-R-2-methylcyclopenta[b]naphth-1-yl)ethane,
- 1-(inden-2-yl)-2-(7-R—R-2,4-dimethylcyclopenta[b]naphth-1-yl)ethane,
- 1-(inden-2-yl)-2-(8-R-6-methylindeno[5,6-d][1,3]dioxol-5-yl)ethane,
- 1-(inden-2-yl)-2-(4-R-2,3,6-trimethylindeno[5,6-b]thien-7-yl)ethane,
- 1-(inden-2-yl)-2-(2-R-4,6-dimethylindeno[5,6-b]thien-7-yl)ethane,
- 1-(inden-2-yl)-2-(4-R-1,2,3,6-tetramethylcyclopenta[f]indol-7-yl)ethane,
- 1-(inden-2-yl)-2-(4-R-1-phenyl-2,3,6-trimethylcyclopenta[/]indol-7-yl)ethane,
- 1-(inden-2-yl)-2-(5-R-7-methylcyclopenta[g]quinol-8-yl)ethane,
- 1-(inden-2-yl)-2-(2-R-5,7-dimethylcyclopenta[g]quinol-8-yl)ethane,
- 1-(4-R-2-methylinden-1-yl)-2-(4-R-2-methyl-5,6,7,8-tetrahydrocyclopenta[b]naphth-1-yl)ethane,
- 1-(4-R-2-methylinden-1-yl)-2-(5-R-2-methyl-6,7,8,9-tetrahydrocyclopenta[a]naphth-3-yl)ethane,
- 1-(4-R-2-methylinden-1-yl)-2-(4-R-2-methylcyclopenta[b]naphth-1-yl)ethane,
- 1-(4-R-2-methylinden-1-yl)-2-(7-R-2,4-dimethylcyclopenta[b]naphth-1-yl)ethane,
- 1-(4-R-2-methylinden-1-yl)-2-(8-R-6-methylindeno[5,6-d][1,3]dioxol-5-yl)ethane,
- 1-(4-R-2-methylinden-1-yl)-2-(4-R-2,3,6-trimethylindeno[5,6-b]thien-7-yl)ethane,
- 1-(4-R-2-methylinden-1-yl)-2-(2-R-4,6-dimethylindeno[5,6-b]thien-7-yl)ethane,
- 1-(4-R-2-methylinden-1-yl)-2-(4-R-1,2,3,6-tetramethylcyclopenta[/]indol-7-yl)ethane,
- 1-(4-R-2-methylinden-1-yl)-2-(4-R-1-phenyl-2,3,6-trimethylcyclopenta[/]indol-7-yl)ethane,
- 1-(4-R-2-methylinden-1-yl)-2-(5-R-7-methylcyclopenta[g]quinol-8-yl)ethane,
- 1-(4-R-2-methylinden-1-yl)-2-(2-R-5,7-dimethylcyclopenta[g]quinol-8-yl)ethane,
- 1-(fluoren-9-yl)-2-(4-R-2-methyl-5,6,7,8-tetrahydrocyclopenta[b]naphth-1-yl)ethane,
- 1-(fluoren-9-yl)-2-(5-R-2-methyl-6,7,8,9-tetrahydrocyclopenta[a]naphth-3-yl)ethane,
- 1-(fluoren-9-yl)-2-(4-R-2-methylcyclopenta[b]naphth-1-yl)ethane,
- 1-(fluoren-9-yl)-2-(7-R-2,4-dimethylcyclopenta[b]naphth-1-yl)ethane,
- 1-(fluoren-9-yl)-2-(8-R-6-methylindeno[5,6-d][1,3]dioxol-5-yl)ethane,
- 1-(fluoren-9-yl)-2-(4-R-2,3,6-trimethylindeno[5,6-b]thien-7-yl)ethane,
- 1-(fluoren-9-yl)-2-(2-R-4,6-dimethylindeno[5,6-b]thien-7-yl)ethane,
- 1-(fluoren-9-yl)-2-(4-R-1,2,3,6-tetramethylcyclopenta[/]indol-7-yl)ethane,
- 1-(fluoren-9-yl)-2-(4-R-1-phenyl-2,3,6-trimethylcyclopenta[/]indol-7-yl)ethane,
- 1-(fluoren-9-yl)-2-(4-R-cyclopenta[b]pyrid-7-yl)ethane,
- 1-(fluoren-9-yl)-2-(5-R-7-methylcyclopenta[g]quinol-8-yl)ethane,
- 1-(fluoren-9-yl)-2-(2-R-5,7-dimethylcyclopenta[g]quinol-8-yl)ethane,
- 1,2-bis[2-(4-R-3-dimethylamino-1,3-benzothiaborollide)]ethane,
- 1,2-bis(4-R-3a,7a-azaborinden-1-yl)ethane,
- 1,2-bis[3-(7-R-2-dimethylamino-1,2-benzothiaborollide)]ethane,
- 1,2-bis[5-(3-R-2-dimethylamino-1,2-thiaborollide)]ethane,
- 1-(cyclopentadienyl)-2-[2-(4-R-3-dimethylamino-1,3-benzothiaborollide)]ethane,
- 1-(cyclopentadienyl)-2-(4-R-3a,7a-azaborinden-1-yl)ethane,
- 1-(cyclopentadienyl)-2-[3-(7-R-2-dimethylamino-1,2-benzothiaborollide)]ethane,
- 1-(cyclopentadienyl)-2-[5-(3-R-2-dimethylamino-1,2-thiaborollide)]ethane,
- 1-(inden-1-yl)-2-[2-(4-R-3-dimethylamino-1,3-benzothiaborollide)]ethane,
- 1-(inden-1-yl)-2-(4-R-3a,7a-azaborinden-1-yl)ethane,
- 1-(inden-1-yl)-2-[3-(7-R-2-dimethylamino-1,2-benzothiaborollide)]ethane,
- 1-(inden-1-yl)-2-[5-(3-R-2-dimethylamino-1,2-thiaborollide)]ethane,
- 1-(inden-2-yl)-2-[2-(4-R-3-dimethylamino-1,3-benzothiaborollide)]ethane,
- 1-(inden-2-yl)-2-(4-R-3a,7a-azaborinden-1-yl)ethane,
- 1-(inden-2-yl)-2-[3-(7-R-2-dimethylamino-1,2-benzothiaborollide)]ethane,
- 1-(inden-2-yl)-2-[5-(3-R-2-dimethylamino-1,2-thiaborollide)]ethane,
- 1-(fluoren-9-yl)-2-[2-(4-R-3-dimethylamino-1,3-benzothiaborollide)]ethane,
- 1-(fluoren-9-yl)-2-(4-R-3a,7a-azaborinden-1-yl)ethane,
- 1-(fluoren-9-yl)-2-[3-(7-R-2-dimethylamino-1,2-benzothiaborollide)]ethane, and
- 1-(fluoren-9-yl)-2-[5-(3-R-2-dimethylamino-1,2-thiaborollide)]ethane.
- Chelating ligands of the formula (II) that are substituted with hydrocarbyl, substituted hydrocarbyl, halocarbyl, or substituted halocarbyl groups in the six-membered ring of indenyl, heteroindenyl or related fluorenyl fragments, or in the five-membered heterocyclic ring of heterocyclopentalenyls, heterocyclopentapentalenyls, or related polycyclic fragments, can be obtained in high yields and/or high purity by the process of the present invention. A particular advantage of the present invention is that readily obtainable and inexpensive compounds of the formula (I) bearing chloroindenyl, bromoindenyl, chlorocyclopenta[b]thienyl, bromocyclopenta[b]thienyl fragments can be used as starting material, thus avoiding the necessity, as in the prior art, of first synthesizing the corresponding substituted indenes to then obtain the desired bridging ligands containing the respective hydrocarbyl, substituted hydrocarbyl, halocarbyl, or substituted halocarbyl substituted indenes and cyclopenta[b]thiophenes. The latter pathway is more time-consuming when the goal is to synthesize libraries of hydrocarbyl, substituted hydrocarbyl, halocarbyl, or substituted halocarbyl substituted bridging ligands of importance for the subsequent synthesis of metallocenes and related organometallic complexes.
- The substituted chelating ligands of the formula (II) prepared according to the present invention can be used in all known applications of the chelating ligands, for example as intermediates for the preparation of transition metal complexes of importance for material chemistry, pharmacy, fine chemicals, organic light-emitting diodes (OLEDs), catalysis and the like.
- The substituted chelating ligands of the formula (II) prepared according to the present invention can be advantageously used for the synthesis of metallocene complexes which are suitable for the polymerization of olefins, in particular α-olefins. These substituted chelating ligands of the formula (II) are preferably used for the synthesis of chiral ansa-bisindenyl metallocenes and related complexes.
- The ansa-bisindenyl metallocenes and related complexes of the present invention contain a metal of Groups 4, 5 or 6, in particular Group 4, of the Periodic Table of the Elements, i.e. titanium, zirconium or hafnium. The metal is preferably zirconium or hafnium, most preferably zirconium.
- The preparation of such ansa-metallocene complexes using the chelating ligands prepared according to the present invention or the chelating ligands of the present invention is carried out by known, customary synthetic methods, for example by the reaction of the chelating ligand (after deprotonation) with suitable transition metal chlorides, for example zirconium tetrachloride or the like. Such synthetic routes are known from the prior art (WO 01/48034).
- In another embodiment this invention relates to:
1. A process for preparing a chelating ligand of the formula (II) from a chelating ligand of the formula (I) via an sp2-sp2 or sp2-sp3 coupling reaction comprising contacting, optionally in the presence of a coupling catalyst, a chelating ligand of the formula (I) with an organometallic compound of the formula (II):
wherein
B is a bridging group that is bonded to L1 and L2 in formula (I) and to L3 and L4 in formula (II);
L1 is a substituted monocyclic or polycyclic ligand that comprises at least one chlorine, bromine, iodine, or sulfonate substituent, directly bonded to an sp2 carbon atom of the ring structure of the ligand;
L2 is a monoanionic ligand; or L2 may, independently, be defined as L1;
L3 is the same group as L1, but said at least one chlorine, bromine, iodine, or sulfonate substituent is replaced with a hydrocarbyl, substituted hydrocarbyl, halocarbyl, or substituted halocarbyl fragment;
L4 is the same group as L2, though, when L2 is defined as L1, L4 may be the same as L3 or L1;
R1 is a hydrocarbyl, substituted hydrocarbyl, halocarbyl, or substituted halocarbyl;
M1 is an element of group 1, 2, 12, 13 or 14 of the Periodic Table of the Elements; each X2, if present, is selected independently from the group consisting of halogen atoms, the hydroxyl group, alkoxy groups, aryloxy groups, mesylate, tosylate and triflate;
r is 1, 2 or 3, and
t is 0, 1 or 2, where r+t corresponds to the oxidation number of M1.
2. The process of paragraph 1 wherein L1 comprises at least one chlorine, bromine, or triflate, preferably at least one bromine or triflate, directly bonded to an sp2 carbon atom of the ring structure of the ligand.
3. The process of paragraph 1 or paragraph 2 wherein L1 is a substituted indenyl, a substituted heteroindenyl, a substituted fluorenyl, or a substituted heterofluorenyl ligand.
4. The process of any preceding paragraph 1 to 3 wherein the coupling catalyst comprises poly(ethylene glycol)triphenylphosphin, polymer bound; dicyclohexylphenylphosphine, polymer-bound; (4-hydroxyphenyl)diphenylphosphine, polymer-bound; triphenylphosphine, polymer-supported; R-(+)-2,2′-bis(diphenylphosphino)-1,1′-binaphthalene, polymer-bound; or S-(−)-2,2′-bis(diphenylphosphino)-1,1′-binaphthalene, polymer bound.
5. The process of any preceding paragraph 1 to 4 wherein L2 is a substituted or unsubstituted monocyclic or polycyclic ligand, preferably L2 is a substituted or unsubstituted cyclopentadienyl ligand, a substituted or unsubstituted heterocyclopentadienyl ligand, a substituted or unsubstituted indenyl ligand, a substituted or unsubstituted heteroindenyl ligand, a substituted or unsubstituted fluorenyl ligand, a substituted or unsubstituted heterofluorenyl ligand.
6. A process for preparing a chelating ligand of the formula (IIa), (IIb), or (IIc) from a chelating ligand of the formula (Ia), (Ib), or (Ic), respectively, and a coupling component of the formula (III),
wherein:
M1 is an element of group 1, 2, 12, 13 or 14 of the Periodic Table of the Elements; the or each X1 is a chlorine, bromine, iodine, triflate, or sulfonate group, and the or each X1 is directly bonded to an sp2 carbon atom of the ring structure of the ligand;
each X2, if present, is selected independently from the group consisting of halogen atoms, the hydroxyl groups, alkoxy groups and aryloxy groups.
R1 is a hydrocarbyl, substituted hydrocarbyl, halocarbyl, or substituted halocarbyl;
R2, R3, R4, and R5′ are, independently, hydrogen, hydrocarbyl, substituted hydrocarbyl, halocarbyl, substituted halocarbyl, silylcarbyl, germylcarbyl radical or polar group as defined above; provided that all R2 groups may be different and, optionally, adjacent R2, R3, R4, and R5′ groups may also together form a cyclic aliphatic or aromatic ring system which may in turn be substituted and may contain heteroatoms; and provided further that R2, R3, and R4 groups are attached to ring carbons; R5′ groups are attached to heteroatoms;
each Q, if present, is, independently, a Group 16 atom, a Group 15 atom, or boron, and preferably S, O, N, or P; when a Q is a Group 15 atom or boron, “q” is one, indicating the presence of one R5′ bonded to Q, and when a Q is a Group 16 atom, “q” is zero, indicating the absence of R5; m, n, and p are independently zero or one, and m+n+p=1; when m or n or p is one, Q is present in the ring as a Group 16 or Group 15 atom or as boron; when m or n or p is zero, Q is absent and is replaced by a ring carbon atom having either a substituent R2 or a substituent X1;
each E, if present, is, independently, a Group 15 atom, preferably N or P; when E is present, it does not have any substituents; m, n, p, and s are independently zero or one, and m+n+p+s=1; when m or n or p or s is one, E is present in the ring as a Group 15 atom; when m or n or p or s is zero, E is absent and is replaced by a ring carbon atom having either a substituent R2 or a substituent X1;
B is a bridging group that contains a Group 13, 14, 15, or 16 element;
A is a substituted or unsubstituted monocyclic or polycyclic ligand;
x represents the number of R2 substituents bonded to the aryl fused to the cyclopentadienyl in structures (Ia) and (IIa), the number of R2 substituents bonded to the 5-member heterocyclic fragment in the structures (Ib) and (IIb), or the number of R2 substituents bonded to the 6-member heterocyclic fragment in the structures (Ic) and (IIc);
x is 0, 1, 2, or 3 in structures (Ia) and (IIa);
x is 0 or 1 in structures (Ib) and (IIb);
x is 0, 1, or 2 in structures (Ic and IIc);
z represents the number of X1 substituents converted to R1 substituents and is 1, 2, 3, or 4 in structures (Ia) and (IIa); 1 or 2 in structures (Ib) and (IIb); and 1, 2, or 3 in structures (Ic) and (IIc);
x+z is 4 in structures (Ia) and (IIa);
x+z is 2 in structures (Ib) and (IIb);
x+z is 3 in structures (Ic) and (IIc);
r is 1, 2 or 3, and
t is 0, 1 or 2, where r+t corresponds to the oxidation number of M1.
7. A process for preparing a chelating ligand of the formula (IId), (IIe), or (IIf) from a chelating ligand of the formula (Id), (Ie), or (If), respectively, and a coupling component of the formula (III),
wherein:
M1 is an element of Group 1, 2, 12, 13 or 14 of the Periodic Table of the Elements;
each X1 is independently a chlorine, bromine, iodine, triflate, or sulfonate group, and each X1 is directly bonded to an sp2 carbon atom of the ring structure of the ligand;
each X2, if present, is selected independently from the group consisting of halogen atoms, the hydroxyl groups, alkoxy groups and aryloxy groups;
R1 is a hydrocarbyl, substituted hydrocarbyl, halocarbyl, or substituted halocarbyl;
R2, R5′, and R6′ are, independently, hydrogen, hydrocarbyl, substituted hydrocarbyl, halocarbyl, substituted halocarbyl, silylcarbyl, germylcarbyl radical or polar group; provided that all R2 groups may be different and, optionally, adjacent R2, R5′, and R6′ groups may also together form a cyclic aliphatic or aromatic ring system which may in turn be substituted and may contain heteroatoms; and provided further that R2 groups are attached to ring carbons; R5′ and R6′ groups are attached to heteroatoms;
B is a bridging group that contains a Group 13, 14, 15, or 16 element;
A is a substituted or unsubstituted monocyclic or polycyclic ligand;
each Q, if present, is independently, a Group 16 atom, a Group 15 atom, or boron, and preferably S, O, N, or P; when a Q is a Group 15 atom or boron, “q” is one, indicating the presence of one R or R6, as the case may be, bonded to Q, and when a Q is a Group 16 atom, “q” is zero, indicating the absence of R5′ or R6′, as the case may be; m, n, p, s, u, and v are independently zero or one, m+n+p=1, and s+u+v=1; when m or n or p or s or u or v is one, Q is present as a Group 16 or a Group 15 atom or as boron; when m or n or p or s or u or v is zero, Q is absent and is replaced by a ring carbon atom having either a substituent R1 or a substituent X1;
each E if present, is, independently, a Group 15 atom, preferably N or P; when E is present it does not have any substituents; m, n, p, s, u, v, w, and y are independently zero or one, m+n+p+s=1, and u+v+w+y=0 or 1; when m or n or p or s or u or v or w or y is present, E is present in the ring as a Group 15 atom; when m or n or p or s or u or v or w or y is zero, E is absent and is replaced by a ring carbon having either a substituent R2 or a substituent X1;
x1+x2 represents the total number of R2 substituents bonded to the fluorenyl ligand instructures (Id) and (IId) or the total number of R2 substituents bonded to the heterofluorenyl ligands in structures (Ie), (If), (IIe) and (IIf);
x1+x2 is 0, 1, 2, 3, 4, 5, 6, or 7 in structures (Id) and (IId);
x1+x2 is 0, 1, 2, or 3 in structures (Ie) and (IIe);
x1+x2 is 0, 1, 2, 3, 4, or 5 in structures (If) and (IIf); z1+z2 represents the total number of X1 substituents converted to R1 substituents and bonded to the fluorenyl ligand in structures (Id) and (IId), or the number of X1 substituents converted to R1 substituents and bonded to the heterofluorenyl ligand in structures (Ie), (If), (IIe), and (IIf);
z1+z2 is 1, 2, 3, 4, 5, 6, 7, or 8 in structures (Id) and (IId);
z1+z2 is 1, 2, 3 or 4 in structures (Ie) and (IIe);
z1+z2 is 1, 2, 3, 4, 5, 6, or 7 in structures (If) and (IIf);
x1+x2+z1+z2 is 8 in structures (Id) and (IId);
x1+x2+z1+z2 is 4 in structures (Ie) and (IIe);
x1+x2+z1+z2 is 6 in structures (If) and (IIf) when u+v+w+y=1;
x1+x2+z1+z2 is 7 in structures (If) and (IIf) when u+v+w+y=0;
r is 1, 2 or 3, and
t is 0, 1 or 2, where r+t corresponds to the oxidation number of M1.
8. The process of paragraph 6 or paragraph 7 wherein the or each X1 is chlorine, bromine, or triflate preferably bromine or triflate.
9. The process of any one of paragraphs 6 to 8 wherein A is a substituted or unsubstituted cyclopentadienyl, a substituted or unsubstituted heterocyclopentadienyl, a substituted or unsubstituted indenyl, a substituted or unsubstituted heteroindenyl, a substituted or unsubstituted fluorenyl, or a substituted or unsubstituted heterofluorenyl.
10. A process for preparing a chelating ligand of the formula (Va), (Vb), (Vc), (Vd), (Ve), (Vf), (Vg), (Vh), (Vi), (Vk), (Vm), (Vn), (Vo), (Vp), (Vq), (Vr), (Vs), (Vt), (Vu), (Vv), (Vw), (Vx), or (Vy) from a chelating ligand of the formula (IVa), (IVb), (IVc), (IVd), (IVe), (IVf), (IVg), (IVh), (IVi), (IVk), (IVm), (IVn), (IVo), (IVp), (IVq), (IVr), (IVs), (IVt), (IVu), (IVv), (IVw), (IVx), or (IVy), respectively, and a coupling component of the formula (III),
wherein:
M1 is an element of group 1, 2, 12, 13 or 14 of the Periodic Table of the Elements;
X3, X4, X5, and X6 are independently selected from chlorine, bromine, iodine, triflate, and sulfonate groups;
each X2, if present, is selected independently from the group consisting of halogen atoms, the hydroxyl groups, alkoxy groups and aryloxy groups;
R1 is a hydrocarbyl, substituted hydrocarbyl, halocarbyl, or substituted halocarbyl;
R3, R4, R5, R6, R7, R8, R9, R10, R11, and R12 are, independently, hydrogen, hydrocarbyl, substituted hydrocarbyl, halocarbyl, substituted halocarbyl, silylcarbyl, germylcarbyl radical or polar group, where, optionally, adjacent R3, R4, R5, R6, R7, R8, R9, R10, R11, R12 groups may also together form a cyclic aliphatic or aromatic ring system which may in turn be substituted and may contain heteroatoms;
B is a bridging group that contains a Group 13, 14, 15, or 16 element;
r is 1, 2 or 3, and
t is 0, 1 or 2, where r+t corresponds to the oxidation number of M1.
11. The process of paragraph 10 wherein X3, X4, X5, and X6 are independently selected from chlorine, bromine, and triflate, preferably from bromine and triflate.
12. A process for preparing a chelating ligand of the formula (VIIa), (VIIb), (VIIc), (VIId), (VIIe), (VIIf), (VIIg), (VIIh), (VIIi), (VIIk), (VIIm), (VIIn), (VIIo), (VIIp), (VIIq), (VIIr), or (VIIs) from a chelating ligand of the formula (VIa), (VIb), (VIc), (VId), (VIe), (VIf), (VIg), (VIh), (VIi), (VIk), (VIn), (VIn), (VIo), (VIp), (VIq), (VIr), or (VIs), respectively, and a coupling component of the formula (III),
wherein:
M1 is an element of Group 1, 2, 12, 13 or 14 of the Periodic Table of the Elements;
X1, X4, X5, and X6 are independently selected from chlorine, bromine, iodine, triflate, and sulfonate groups;
each X2, if present, is selected independently from the group consisting of halogen atoms, the hydroxyl groups, alkoxy groups and aryloxy groups;
R1 is a hydrocarbyl, substituted hydrocarbyl, halocarbyl, or substituted halocarbyl;
R3, R4, R5, R6, R7, R8, R9, and R10 are, independently, hydrogen, hydrocarbyl, substituted hydrocarbyl, halocarbyl, substituted halocarbyl, silylcarbyl, germylcarbyl radical or polar group, where, optionally, adjacent R3, R4, R5, R6, R7, R8, R9, and R10 groups may also together form a cyclic aliphatic or aromatic ring system which may in turn be substituted and may contain heteroatoms;
B is a bridging group that contains a Group 13, 14, 15, or 16 element;
r is 1, 2 or 3; and
t is 0, 1 or 2, where r+t corresponds to the oxidation number of M1.
13. The process of paragraph 12 wherein X3, X4, X5, and X6 are independently selected from chlorine, bromine, and triflate, preferably from bromine and triflate.
14. A process for preparing a chelating ligand of the formula (IXa), (IXb), (IXc), (IXd), (IXe), (IXf), (IXg), (IXh), (IXi), or (IXk) from a chelating ligand of the formula (VIIIa), (VIIIb), (VIIIc), (VIIId), (VIIIe), (VIIIf), (VIIIg), (VIIIh), (VIIIi), or (VIIk), respectively, and a coupling component of the formula (III),
wherein:
M1 is an element of Group 1, 2, 12, 13 or 14 of the Periodic Table of the Elements;
X3 and X4 are, independently, chlorine, bromine, iodine, triflate, or sulfonate groups;
each X2, if present, is selected independently from the group consisting of halogen atoms, the hydroxyl groups, alkoxy groups and aryloxy groups;
R1 is a hydrocarbyl, substituted hydrocarbyl, halocarbyl, or substituted halocarbyl;
R3, R4, R5, R6, R7, R8, R9, R10, R11, R12 are, independently, hydrogen, hydrocarbyl, substituted hydrocarbyl, halocarbyl, substituted halocarbyl, silylcarbyl, germylcarbyl radical or polar group, where, optionally, adjacent R3, R4, R5, R6, R7, R8, R9, R10, R11, R12 groups may also together form a cyclic aliphatic or aromatic ring system which may in turn be substituted and may contain heteroatoms;
B is a bridging group that contains a Group 13, 14, 15, or 16 element;
r is 1, 2 or 3, and
t is 0, 1 or 2, where r+t corresponds to the oxidation number of M1.
15. The process of paragraph 14 wherein X3 and X4 are, independently, chlorine, bromine, or triflate, preferably bromine or triflate.
16. The process of any preceding paragraph 1 to 15 wherein M1 is Li, Na, K, Rb, Cs, Be, Mg, Ca, Sr, Ba, B, Si, Sn, Zn, Cd or Hg.
17. The process of any preceding paragraph 1 to 16 wherein M1 is B, Si, Sn, Zn, Cd or Hg.
18. The process of any preceding paragraph 1 to 17 wherein M1 is B, Sn or Zn.
19. The process of any preceding paragraph 1 to 18 wherein t is 1 or 2 and each X2 is selected independently from the group consisting of halogen atoms, the hydroxyl group, alkoxy and aryloxy.
20. The process of any preceding paragraph 1 to 19 wherein B is a bridging group containing boron or a Group 14, 15 or 16 element.
21. The process of any preceding paragraph 1 to 20 wherein B selected from R′2C, R′2Si, R′2Ge, R′2CCR′2, R′2CCR′2CR′2, R′2CCR′2CR′2CR′2, R′C═CR′, R′C═CR′CR′2, R′2CCR′═CR′CR′2, R′C═CR′CR′═CR′, R′C═CR′CR′2CR′2, R′2CSiR′2, R′2SiSiR′2, R′2CSiR′2CR′2, R′2SiCR′2SiR′2, R′C═CR′SiR′2, R′2CGeR′2, R′2GeGeR′2, R′2CGeR′2CR′2, R′2GeCR′2GeR′2, R′2SiGeR′2, R′C═CR′GeR′2, R′B, R′2C—BR′, R′2C—BR′—CR′2, R′2CCR′2, R′2CR′2C—O CR′2CR′2, R′2CCR′2CR′2, R′2C—OR′═CR′, R′2C—S—CR′2, R′2CR′2C—S—CR′2CR′2, R′2C—S—CR′2CR′2, R′2C—S—CR′═CR′, R′2C—Se—CR′2, R′2CR′2C—Se—CR′2CR′2, R′2C—Se—CR′2CR′2, R′2C—Se—CR′═CR′, R′2C—N═CR′, R′2C—NR′—CR′2, R′2C—NR′—CR′2CR′2, R′2C—NR′—CR′═CR′, R′2CR′2C—NR′—CR′2CR′2, R′2C—P═CR′, and R′2C—PR′—CR12 where R′is hydrogen or a C1-C20 containing hydrocarbyl, substituted hydrocarbyl, halocarbyl, substituted halocarbyl, silylcarbyl or germylcarbyl substituent and optionally two or more adjacent R′ may join to form a substituted or unsubstituted, saturated, partially unsaturated or aromatic, cyclic or polycyclic substituent.
22. The process of any preceding paragraph 1 to 21 wherein B is selected from CH2, CH2CH2, CH(CH3)2, SiMe2, SiPh2, SiMePh, Si(CH2)3, and Si(CH2)4.
23. The process of any preceding paragraph 1 to 22 wherein the reaction is conducted in the presence of a transition metal-containing catalyst.
24. The process of paragraph 23 wherein the transition metal is selected from Groups 8 to 10 of the Periodic Table of the Elements.
25. A method of synthesizing a metallocene complex, the method comprising using a chelating ligand prepared by the process of any preceding paragraph 1 to 24.
26. A process for polymerizing olefins comprising contacting a catalyst system comprising a metallocene complex synthesized by the method of paragraph 25 with at least one olefin. - All manipulations with air and moisture sensitive compounds were performed either in an atmosphere of thoroughly purified argon using a standard Schlenk technique or in a controlled atmosphere Glove Box (Vacuum Atmospheres Co.). Tetrahydrofuran (THF, Merck=Merck KGaA, Darmstadt, Germany) and diethyl ether (Merck) for synthesis were purified by distillation over LiAlH4, and stored over sodium benzophenone ketyl under an inert atmosphere; prior to use, the solvents were distilled from the benzophenone ketyl. Hydrocarbon solvents such as benzene (Merck), toluene (Merck) and hexanes (Merck) and including benzene-d6 for NMR measurements were typically distilled over CaH2, and were stored over Na/K alloy under an inert atmosphere; prior to use, the solvents were distilled from the Na/K alloy. Methylene chloride (Merck) and CCl2D2 (Cambridge Isotope) for NMR measurements were distilled and stored over CaH2 under an inert atmosphere; prior to use, the solvents were distilled from the CaH2. Benzothiophene (Aldrich), 2.5 M nBuLi in hexanes (Acros=Acros Organics), 1.6 M MeLi in ether (Acros), 3.0 M methylzinc chloride in THF (Aldrich), 1.0 M phenylmagnesium bromide in THF (Aldrich), 1.0 M p-tolylmagnesium bromide in THF (Aldrich), 1.0 M mesityl bromide in THF (Aldrich), 0.5 M 4-N,N-dimethylaminophenylmagnesium bromide in THF (Aldrich), 2-bromobenzylbromide (Aldrich), 2-chlorobenzylchloride (Merck), diethyl methylmalonate (Acros), 2-bromobenzotrifluoride (Acros), 3-bromobenzotrifluoride (Acros), 1,3-bis(trifluoromethyl)-5-bromobenzene (Aldrich), 4-tert-butylbromobenzene (Acros), 2-bromo-4-isopropylaniline (Aldrich), 2-bromo-2-methylpropanoyl bromide (Aldrich), 1-bromonaphthalene (Acros), 0.5 M ZnCl2 in THF (Aldrich), and Pd(PtBu3)2 (Strem=Strem Chemical Co.), 2-[di(tert-butyl)phosphino]-1,1′-biphenyl (Strem), ZrCl4(THF)2 (Aldrich), NaBH4 (Acros), NaBPh4 (Aldrich), anhydrous powdered AlCl3 (Merck), and dichlorodimethylsilane (Merck) were used as obtained. Solutions of Grignard reagents (2-trifluoromethylphenylmagnesium bromide, 3-trifluoromethylphenylmagnesium bromide, 4-tert-butylphenylmagnesium bromide, 1,3-bis(trifluoromethyl)-5-bromobenzene, and 1-naphthylmagnesium bromide) in THF were obtained from magnesium turnings (Aldrich) and the respective arylbromides in THF at reflux. 5-Methyl-4,5-dihydro-6H-cyclopenta[b]-thiophen-6-one [Ryabov, A. N.; Gribkov, D. V.; Izmer, V. V.; Voskoboynikov, A. Z. Organometallics 2002, 21, 2842] was prepared according to the published method. 2-Bromo-1-(bromomethyl)-3-methylbenzene [Baker, R. W.; Foulkes, M. A.; Griggs, M.; Nguyen, B. N. Tetrahedron Lett. 2002, 43, 9319] was prepared from 2-bromo-m-xylene (Acros) according to the published procedure. Pd(dba)2 was prepared from PdCl2 (Aldrich) and dibenzolidenacetone (Acros) as described in literature [Coulson, D. R. Inorg. Synth. 1972, 13, 121].
- 1H and 13C NMR spectra were recorded with a Varian VXR 400 or Brucker DPX-300 for 0.1-5% solutions in deuterated solvents. Chemical shifts for 1H and 13C were measured relative to TMS. In 1H NMR spectra, the assignment was made on the evidence of double resonance and NOE experiments. C, H microanalyses were done using CHN—O-Rapid analyzer (Heracus).
-
- In a three-necked round-bottom 2000 ml flask equipped with a reflux condenser, dropping funnel with pressure-equalizing, and magnetic stirring bar 20.5 g (0.89 mol) of sodium metal were dissolved in 450 ml of dry ethanol. To the resulting solution 155 g (0.89 mol) of diethylmethylmalonate in 150 ml of dry ethanol were added dropwise within 15 min. This mixture was stirred for 15 min; then, 186 g (0.89 mol) of o-bromobenzyl bromide were added, while vigorously stirring, at a rate that allowed the reaction mixture to maintain a gentle reflux. This mixture was further refluxed for 4 hours and cooled to room temperature. A solution of 151 g of potassium hydroxide in 400 ml of water was added. The resulting mixture was refluxed for 3 hours to saponificate the ester formed. Ethanol and water were distilled off. To the residue 500 ml of water and, then, 12 M HCl (to pH 1) were added. The substituted methylmalonic acid precipitate was separated, washed with 2×200 ml of cold water, and dried overnight on a watch glass. Crude 3-(2-bromophenyl)-2-methylpropanoic acid was obtained after decarboxilation of this substituted methylmalonic acid by heating it at 160° C. for 2 hours. The product was used without further purification. Mixture of this acid and 160 ml of SOCl2 was stirred for 24 hours at ambient temperature. Thionyl chloride was distilled off. The crude 3-(2-bromophenyl)-2-methylpropanoyl chloride was dissolved in 270 ml of CH2Cl2 and was added dropwise, while vigorously stirring, to a suspension of 136 g (1.02 mol) of AlCl3 in 1350 ml of CH2Cl2 over a period of 1 hour at 0° C. Then, this mixture was refluxed for 3 hours, cooled to ambient temperature, and poured on 500 cm3 of ice. The organic layer was separated. The aqueous layer was extracted with 3×300 ml of methyl-tert-butyl ether. The combined organic fractions were dried over K2CO3 and evaporated to dryness. Fractional distillation gave the title indanone, b.p. 131-134° C./2 mm Hg. Yield 125.5 g (75%) of colorless solid.
- Anal. calc. for C10H9BrO: C, 53.36; H, 4.03. Found: C, 53.19; H, 3.98.
- 1H NMR (CDCl3): δ 7.76 (d, J=7.6 Hz, 1H, 7-H), 7.71 (d, J=7.6 Hz, 1H, 5-H), 7.28 (t, J=7.6 Hz, 1H, 6-H), 3.36 (dd, J=17.5 Hz, J=7.6 Hz, 1H, 3-H), 2.70-2.82 (m, 1H, 2-H), 2.67 (dd, J=17.5 Hz, J=3.8 Hz, 1H, 3′-H), 1.34 (d, J=7.3 Hz, 3H, 2-Me).
- 13C{1H} NMR (CDCl3): δ 208.3, 152.9, 138.2, 137.2, 129.0, 122.6, 122.0, 41.8, 35.7, 16.0.
-
- To a solution of 116 g (0.52 mol) of 4-bromo-6-chloro-2-methyl-1-indanone in 950 ml of THF-methanol (2:1, vol.) 38.3 g (1.02 mol) of NaBH4 were added in small portions for 2 hours at −5° C. (Caution: temperature must be lower than 0° C.). The mixture was stirred overnight at ambient temperature. The resulting mixture was poured over 1000 cm3 of ice and acidified with 10% HCl to pH=4. The organic layer was separated; the aqueous layer was extracted with 3×300 ml of methyl-tert-butyl ether. The combined organic fractions were dried over K2CO3 and evaporated to dryness. To the residue 1500 ml of toluene were added. This toluene solution was treated with a catalytic amount of pTolSO3H (ca. 2 g) for 2 hours at reflux. Then this mixture was cooled to room temperature and passed through a short Silica Gel 60 column (40-63 μm, d 60 mm, 140 mm). This column was additionally eluted with 250 ml of toluene. The chromatographed product was evaporated to dryness. Fractional distillation gave the title indene, b.p. 104-108° C./5 mm Hg. Yield 100 g (93%) of colorless solid.
- Anal. calc. for C10H9Br: C, 57.44; H, 4.34. Found: C, 57.59; H, 4.40.
- 1H NMR (CDCl3): δ 7.23 (dd, J=7.9 Hz, J=1.0 Hz, 1H, 6-H), 7.18 (dd, J=7.4 Hz, J=1.0 Hz, 1H, 4-H), 7.10 (m, 1H, 5-H), 6.51 (m, 1H, 3-H), 3.28 (m, 2H, 1,1′-H), 2.17 (s, 3H, 2-Me).
- 13C{1H} NMR (CDCl3): δ 147.3, 146.8, 143.3, 128.2, 127.1, 126.6, 118.7, 118.3, 44.2, 16.7.
-
- In an argon atmosphere, to a solution of 10.0 g (47.8 mmol) of 2-methyl-7-bromoindene in 250 ml of diethyl ether, 29.9 ml of 1.6 M MeLi (47.8 mmol) in ether was added at 10° C. This mixture was stirred for 1 hour at 20° C. and, then, cooled to 0° C. At this temperature, 2.89 ml (3.08 g, 23.9 mmol) of Me2SiCl2 was added. The resulting mixture was stirred for 2 hours at ambient temperature; then 100 ml of water was added. The organic layer was separated, dried over K2CO3, and evaporated to dryness. The residue was treated with 25 ml of hexanes. The white solid that precipitated was filtered off, washed with 3×30 ml of hexanes, and dried in vacuum. Yield 5.37 g (47%) of white solid of ca. 1 to 1 mixture of rac- and meso-compounds.
- Anal. calc. for C22H22Br2Si: C, 55.71; H, 4.68. Found: C, 56.02; H, 4.77.
- 1H NMR (CDCl3): δ 7.36 (d, J=8.5 Hz, 2H, 5,5′-H in rac- or meso-compound), 7.34 (d, J=8.5 Hz, 2H, 5,5′-H in meso- or rac-compound), 7.32 (d, J=7.6 Hz, 2H, 7,7′-H in rac- or meso-compound), 7.23 (d, J=7.6 Hz, 2H, 7,7′-H in meso- or rac-compound), 6.95 (t, J=8.1 Hz, 2H, 6,6′-H in rac- or meso-compound), 6.93 (t, J=8.1 Hz, 2H, 6,6′-H in meso- or rac-compound), 6.70 (br.s, 4H, 3,3′-H in rac- and meso-compounds), 3.74 (s, 2H, CHSi, CHSi′ in rac- or meso-compound), 3.73 (s, 2H, CHSi, CHSi′ in meso- or rac-compound) 2.23 (d, 6H, J=1.2 Hz, 2,2′-Me in rac- or meso-compound), 2.17(d, 6H, J=1.2 Hz, 2,2′-Me in meso- or rac-compound), −0.19 (s, 3H, SiMe in meso-compound), −0.24 (s, 6H, SiMe2 in rac-compound), −0.27 (s, 3H, SiMe′ in meso-compound).
- 13C{1H} NMR (CDCl3): δ 148.4, 148.3, 145.9*, 145.1, 145.0, 128.4*, 126.5*, 124.2, 124.1, 121.8*, 114.1*, 48.6, 48.5, 17.9*, −5.4*, −5.6 (* two resonance of rac- and meso-isomers).
-
- In a 2000 ml three-necked round-bottom flask equipped with a reflux condenser, dropping funnel with pressure-equalizing, and magnetic stirring bar, 19.5 g (0.87 mol) of sodium metal was dissolved in 480 ml of dry ethanol. To the resulting solution, 141 g (0.84 mol) of diethylmethylmalonate in 150 ml of dry ethanol was added dropwise within 15 min. This mixture was stirred for 15 min; then, 108 ml (138 g, 086 mol) of o-chlorobenzyl chloride was added, while vigorously stirring, at a rate that allowed the reaction mixture to maintain a gentle reflux. This mixture was further refluxed for 4 hours and, then, cooled to room temperature. A solution of 168 g of potassium hydroxide in 450 ml of water was added. The resulting mixture was refluxed for 3 hours to saponificate the ester formed. Ethanol and water were distilled off. To the residue, 500 ml of water and, then, 12 M HCl (to pH 1) were added. The substituted methylmalonic acid precipitate was separated, washed with 2×200 ml of cold water, and dried in vacuum. Crude 3-(2-chlorophenyl)-2-methylpropanoic acid was obtained after decarboxylation of the substituted methylmalonic acid by heating it at 180° C. for 2 hours. This product was used without further purification. A mixture of this acid with 210 ml of SOCl2 was stirred for 24 hours at ambient temperature. Thionyl chloride was distilled off. Fractional distillation gave 147 g of a colorless oil, 3-(2-chlorophenyl)-2-methylpropanoyl chloride, b.p. 115-117° C./7 mm Hg. This acid chloride was dissolved in 300 ml of CH2Cl2 and was added dropwise, while vigorously stirring, to a suspension of 170 g (1.28 mol) of AlCl3 in 1500 ml of CH2Cl2 over a period of 2 hours at 0° C. Then, this mixture was refluxed for 3 hours, cooled to ambient temperature, and poured over 500 cm3 of ice. The organic layer was separated. The aqueous layer was extracted with 3×300 ml of methyl-tert-butyl ether. The combined organic fractions were dried over K2CO3 and evaporated to dryness. Fractional distillation gave 106 g (76%) of 4-chloro-2-methyl-1-indanone, b.p. 128° C./10 mm Hg.
- Anal. calc. for C10H9ClO: C, 66.49; H, 5.02. Found: C, 66.32; H, 4.95.
- 1H NMR (CDCl3): δ 7.60 (m, 1H, 7-H), 7.52 (dd, J=7.8 Hz, J=0.9 Hz, 1H, 5-H), 7.29 (m, 1H, 6-H), 3.35 (m, 1H, 2-H), 2.69 (m, 2H, CH2), 1.30 (d, 3H, Me).
- 13C NMR (CDCl3): δ 207.5, 150.4, 137.7, 133.6, 132.2, 128.4, 121.6, 41.3, 33.3, 15.5.
-
- To a solution of 106 g (0.59 mol) of 4-chloro-2-methyl-1-indanone in 1000 ml of THF-methanol (2:1, vol.) 48.4 g (1.29 mol) of NaBH4 were added in small portions over a period of 2 hours at −5° C. (Caution: temperature must be lower than 0° C.). The mixture was stirred for 12 hours at ambient temperature and, then, poured over 1000 cm3 of ice, and acidified with 10% HCl to pH=4. The organic layer was separated. The aqueous layer was extracted with 3×300 ml of methyl-tert-butyl ether. The combined organic fractions were dried over K2CO3 and evaporated to dryness. To the yellowish oil obtained 1500 ml of toluene were added. This toluene solution was treated with a catalytic amount of pTolSO3H (ca. 2 g) for 2 hours at reflux. Then, the mixture was cooled to room temperature and passed through a short Silica Gel 60 column (40-63 μm, d 80 mm, 150 mm). This column was additionally eluted with 500 ml of toluene. The chromatographed product was evaporated to dryness. Fractional distillation gave the chloro-substituted indenes, b.p. 120-125° C./10 mm Hg. Yield 89.9 g (97%) of colorless oil of ca. 1 to 9 mixture of 4-chloro-2-methylindene and 7-chloro-2-methylindene.
- Anal. calc. for C10H9Cl: C, 72.96; H, 5.51. Found: C, 72.80; H, 5.47.
- 1H NMR (CDCl3): 4-chloro-2-methylindene, δ 7.14-7.31 (m, 3H, 5,6,7-H), 6.72 (m, 1H, 3-H), 3.38 (m, 2H, 1,1′-H), 2.23 (s, 3H, 2-Me); 7-chloro-2-methylindene, □ 7.14-7.31 (m, 3H, 4,5,6-H), 6.53 (m, 1H, 3-H), 3.36 (m, 2H, 1,1′-H), 2.23 (s, 3H, 2-Me).
- 13C NMR (CDCl3): 7-chloro-2-methylindene, δ 147.9, 147.2, 141.3, 129.7, 128.3, 127.4, 124.1, 118.5, 42.6, 17.0.
-
- In argon atmosphere to a solution of 6.15 g (37.4 mmol) of 2-methyl-4/7-chloroindenes in 200 ml of diethyl ether, 23.4 ml of 1.6 M MeLi (37.4 mmol) in ether was added at 0° C. This mixture was stirred for 2 hour at 20° C. and, then, cooled to 0° C. At this temperature, 2.26 ml (2.41 g, 18.7 mmol) of Me2SiCl2 was added. The resulting mixture was stirred for 2 hours at ambient temperature; then 100 ml of water was added. The organic layer was separated, dried over K2CO3, and evaporated to dryness. The residue was re-crystallized from hexanes. Yield 5.37 g (69%) of white solid of ca. 1 to 1 mixture of rac- and meso-compounds.
- Anal. calc. for C22H22Cl2Si: C, 68.56; H, 5.75. Found: C, 68.70; H, 5.88.
- 1H NMR (CDCl3): δ 7.18 (m, 2H, 5,5′-H in rac- or meso-compound), 7.15 (m, 2H, 5,5′-H in meso- or rac-compound), 7.09 (d, J=7.9 Hz, 2H, 7,7′-H in rac- or meso-compound), 7.07 (d, J=7.9 Hz, 2H, 7,7′-H in meso- or rac-compound), 6.90 (m, 6,6′-H in rac- or meso-compound), 6.88 (m, 2H, 6,6′-H in meso- or rac-compound), 6.63 (m, 4H, 3,3′-H in rac- and meso-compounds), 3.59 (m, 2H, CHSi, CHSi′ in rac- or meso-compound), 3.58 (m, 2H, CHSi, CHSi′ in meso- or rac-compound), 2.11 (d, 6H, J=1.0 Hz, 2,2′-Me in rac- or meso-compound), 2.06(d, 6H, J=1.0 Hz, 2,2′-Me in meso- or rac-compound), −0.33 (s, 3H, SiMe in meso-compound), −0.38 (s, 6H, SiMe2 in rac-compound), −0.40 (s, 3H, SiMe′ in meso-compound).
- 13C{1H} NMR (CDCl3): δ 148.31, 148.24, 146.1*, 143.15, 143.05, 128.0, 126.3, 125.3*, 124.6*, 123.88, 123.82, 121.3, 48.3, 48.2, 17.9*, −5.52, −5.59, −5.8 (* two resonance of rac- and meso-isomers).
-
- In an argon atmosphere, to a solution of 15 mL of THF with 29.0 ml of 0.5 M ZnCl2 (14.5 mmol) in THF 13.0 ml of 1.0 M phenylmagnesium bromide (13.0 mmol) in THF was added at ambient temperature. This mixture was stirred for 1 hour, and, then, 10.0 ml of 0.02 M Pd(PtBu3)2 (0.20 mmol, 4 mol. %) in THF and 2.37 g (5.0 mmol) of 1 were added. The resulting mixture was stirred for 5 hours at reflux. The product was isolated by flash chromatography on Silica Gel 60 (40-63 μm, d 30 mm, l 100 mm; eluent: hexanes). Yield 2.27 g (97%) of white solid of ca. 1 to 1 mixture of rac- and meso-compounds.
- Anal. calc. for C34H32Si: C, 87.13; H, 6.88. Found: C, 87.30; H, 6.93.
- 1H NMR (CDCl3): δ 7.60-7.16 (m, 18H, 5,5′,6,6′,7,7′-H in indenyl and Ph in rac- and meso-compounds), 6.84 (m, 2H, 3,3′-H in indenyl of rac- or meso-compound), 6.82 (m, 2H, 3,3′-H in indenyl of meso- or rac-compound), 3.83 (s, 4H, 1,1′-H in indenyl of rac- and meso-compounds), 2.27 (d, J=0.9 Hz, 6H, 2,2′-Me in rac- or meso-compound), 2.19 (d, J=0.9 Hz, 6H, 2,2′-Me in meso- or rac-compound), −0.150 (s, 3H, SiMe in meso-compound), −0.152 (s, 6H, SiMe2 in rac-compound), −0.17 (s, 3H, SiMe′ in meso-compound).
13C{1H} NMR (CDCl3): δ 147.7, 147.6, 145.52, 145.48, 143.0, 142.9, 141.40, 141.36, 134.2*, 128.9*, 128.4*, 126.7*, 126.05, 126.00, 125.60, 125.58, 123.11, 123.05, 122.19, 122.14, 47.7, 47.6, 18.0, 17.9, −5.57*, −5.60 (* two resonance of rac- and meso-isomers). - In an argon atmosphere, a mixture of 1.75 g (5.1 mmol) of NaBPh4, 2.37 g (5.0 mmol) of 1, 10.0 ml of 0.02 M Pd(PtBu3)2 (0.20 mmol, 4 mol. %) in THF, and 50 ml of THF were stirred for 15 hours at reflux. The product was isolated by flash chromatography on Silica Gel 60 (40-63 μm, d 30 mm, l 100 mm; eluent: hexanes). Yield 2.30 g (98%) of white solid of ca. 1 to 1 mixture of rac- and meso-compounds.
- Anal. calc. for C34H32Si: C, 87.13; H, 6.88. Found: C, 87.38; H, 6.80.
-
- In the Glove Box, to a solution of 2.15 g (4.6 mmol) of 1a in 100 ml of ether, 3.7 ml of 2.5M nBuLi (9.2 mmol) in hexanes was added at ambient temperature. This mixture was stirred for 24 hours and, then, cooled to −78° C.; 1.74 g (4.6 mmol) of ZrCl4(THF)2 was added. The resulting mixture was stirred for 24 hours at room temperature and, then, evaporated to dryness. To the residue 100 ml of toluene was added. This mixture was stirred for 8 hours at 90° C. The hot solution was filtered through a glass frit (G4). The residue was additionally washed with 5×70 ml of hot toluene. The filtrate was evaporated to dryness. The solid obtained was recrystallized from dichloromethane. Yield 1.04 g (36%) of orange crystalline solid.
- Anal. calc. for C34H30Cl2SiZr: C, 64.94; H, 4.81. Found: C, 65.11; H, 4.92.
- 1H NMR (CD2Cl2): δ 7.66 (m, 2H, 7,7′-H of indenyl), 7.62 (m, 2H, 4,4′-H of Ph), 7.58 (dd, J=6.9 Hz, J=1.5 Hz, 2H, 5,5′-H of indenyl), 7.40 (m, 4H, 3,3′,5,5′-H of Ph), 7.33 (m, 2H, 2,2′,6,6′-H of Ph), 7.09 (dd, J=8.7 Hz, J=6.9 Hz, 2H, 6,6′-H of indenyl), 6.88 (m, 2H, 3,3′-H of indenyl), 2.21 (d, J=0.5 Hz, 6H, 2,2′-Me of indenyl), 1.32 (s, 6H, SiMe2).
-
- In an argon atmosphere, to a solution of 15 mL of THF with 34.0 ml of 0.5 M ZnCl2 (17.0 mmol) in THF, 15.2 ml of 1.0 M p-tolylmagnesium bromide (15.2 mmol) in THF was added at ambient temperature. This mixture was stirred for 1 hour, and, then, 11.7 ml of 0.02 M Pd(PtBu3)2 (0.23 mmol, 4 mol. %) in THF and 2.78 g (5.86 mmol) of 1 were added. The resulting mixture was stirred for 5 hours at reflux. The product was isolated by flash chromatography on Silica Gel 60 (40-63 μm, d 30 mm, l 100 mm; eluent: hexanes). Yield 2.79 g (96%) of white solid of ca. 1 to 1 mixture of rac- and meso-compounds.
- Anal. calc. for C36H36Si: C, 87.04; H, 7.30. Found: C, 87.22; H, 7.39.
- 1H NMR (CDCl3): δ 7.45-7.51 (m, 6H, 7,7′-H in indenyl of rac-compound and 3,3′,5,5′-H in p-tolyl of rac- and meso-compounds), 7.38 (m, 2H, 7,7′-H in indenyl of meso-compound), 7.27-7.32 (m, 12H, 5,5′-H in indenyl and 2,2′,6,6′-H in p-tolyl of rac- and meso-compounds), 7.16-7.22 (m, 4H, 6,6′-H in indenyl of rac- and meso-compounds), 6.84 (m, 2H, 3,3′-H in indenyl of meso-compound), 6.82 (m, 2H, 3,3′-H in indenyl of rac-compound), 3.82 (s, 4H, 1,1′-H in indenyl rac- and meso-compounds), 2.46 (s, 6H, 4,4′-Me in p-tolyl of rac-compound), 2.45 (s, 6H, 4,4′-Me in p-tolyl of meso-compound), 2.27 (d, J=0.9 Hz, 6H, 2,2′-Me in indenyl of meso-compound), 2.19 (d, J=0.9 Hz, 6H, 2,2′-Me in indenyl of rac-compound), −0.15 (s, 9H, SiMe2 in rac-compound and SiMe in meso-compound), −0.17 (s, 3H, SiMe′ in meso-compound).
- 13C{1H} NMR (CDCl3): δ 147.6, 147.4, 145.47, 145.42, 143.0, 142.9, 136.46, 136.41, 136.39, 136.35, 134.1 (two resonances), 129.1 (two resonances), 128.8 (two resonances), 126.1, 126.0, 125.49, 125.46, 123.1, 123.0, 122.0, 121.9, 47.6, 47.5, 21.2 (two resonances), 18.0, 17.9, −5.7 (br.s, three resonances).
- In an argon atmosphere, to a solution of 20 mL of THF with 22.7 ml of 0.5 M ZnCl2 (11.3 mmol) in THF, 10.1 ml of 1.0 M p-tolylmagnesium bromide (10.1 mmol) in THF was added at ambient temperature. This mixture was stirred for 1 hour, and, then, 86.3 mg (0.15 mmol, 4 mol. %) of Pd(dba)2, 89.5 mg (0.30 mmol) of 2-di-tert-butylphosphinobiphenyl, and 1.85 g (3.91 mmol) of 1-Cl were added. The resulting mixture was stirred for 15 hours at reflux. The product was isolated by flash chromatography on Silica Gel 60 (40-63 μm, d 30 mm, l 100 mm; eluent: hexanes). Yield 1.59 g (82%) of white solid of ca. 1 to 1 mixture of rac- and meso-compounds.
- Anal. calc. for C36H36Si: C, 87.04; H, 7.30. Found: C, 87.14; H, 7.25.
-
- In the Glove Box, to a solution of 2.48 g (5.0 mmol) of 1b in 100 ml of ether, 4.0 ml of 2.5M nBuLi (10.0 mmol) in hexanes was added at ambient temperature. This mixture was stirred for 24 hours and, then, cooled to −78° C.; 1.89 g (5.0 mmol) of ZrCl4(THF)2 was added. The resulting mixture was stirred for 24 hours at room temperature and, then, evaporated to dryness. To the residue 100 ml of toluene was added. This mixture was stirred for 8 hours at 90° C. The hot solution was filtered through a glass frit (G4). The residue was additionally washed with 3×50 ml of hot toluene. The filtrate was evaporated to dryness. The solid obtained was recrystallized from dichloromethane. Yield 0.92 g (28%) of orange crystalline solid.
- Anal. calc. for C36H34Cl2SiZr: C, 65.83; H, 5.22. Found: C, 65.97; H, 5.04.
- 1H NMR (CD2Cl2): δ 7.63 (d, J=8.7 Hz, 2H, 7,7′-H of indenyl), 7.46 (m, 4H, 2,2′,6,6′-H of p-tolyl), 7.30 (d, J=7.0 Hz, 2H, 5,5′-H of indenyl), 7.21 (m, 4H, 3,3′,5,5′-H of p-tolyl), 7.06 (dd, J=8.7 Hz, J=7.0 Hz, 2H, 6,6′-H of indenyl), 6.86 (s, 2H, 3,3′-H of indenyl), 2.33 (s, 6H, 4,4′-Me of p-tolyl), 2.20 (s, 6H, 2,2′-Me of indenyl), 1.30 (s, 6H, SiMe2).
-
- In an argon atmosphere, to a solution of 15 mL of THF with 29.0 ml of 0.5 M ZnCl2 (14.5 mmol) in THF. 13.0 ml of 1.0 M mesitylmagnesium bromide (13.0 mmol) in THF was added at ambient temperature. This mixture was stirred for 1 hour, and, then, 10.0 ml of 0.02 M Pd(PtBu3)2 (0.20 mmol, 4 mol. %) in THF and 2.51 g (5.0 mmol) of 1 were added. The resulting mixture was stirred for 5 hours at reflux. The product was isolated by flash chromatography on Silica Gel 60 (40-63 μm, d 30 mm, l 100 mm; eluent: hexanes). Yield 2.60 g (94%) of white solid of ca. 1 to 1 mixture of rac- and meso-compounds.
- Anal. calc. for C40H44Si: C, 86.90; H, 8.02. Found: C, 87.17; H, 8.10.
- 1H NMR (CDCl3): δ 7.72 (d, J=7.5 Hz, 2H, 7,7′-H in indenyl of rac- or meso-compound), 7.49 (d, J=7.5 Hz, 2H, 7,7′-H in indenyl of meso- or rac-compound), 7.29 (t, J=7.5 Hz, 2H, 6,6′-H in indenyl of rac- or meso-compound), 7.24 (t, J=7.5 Hz, 2H, 6,6′-H in indenyl of meso- or rac-compound), 7.05-7.13 (m, 12H, 6,6′-H in indenyl and 3,3′,5,5′-H in mesityl of rac- and meso-compounds), 6.31 (s, 4H, 3,3′-H in indenyl of rac- and meso-compounds), 4.03 (s, 2H, 1,1′-H in indenyl of rac- or meso-compound), 4.00 (s, 2H, 1,1′-H in indenyl of meso- or rac-compound), 2.45 (s, 12H, 2,6-Me in mesityl of rac- or meso-compound), 2.34 (d, J=0.9 Hz, 6H, 2,2′-Me in indenyl of rac- or meso-compound), 2.23 (d, J=0.9 Hz, 6H, 2,2′-Me in indenyl of meso- or rac-compound), 2.11 (s, 6H, 4,4′-H in mesityl of rac- or meso-compound), 2.10 (s, 6H, 4,4′-H in mesityl of meso- or rac-compound), 2.07 (s, 12H, 2,6-Me in mesityl of meso- or rac-compound), −0.22 (s, 3H, SiMe of meso-compound), −0.246 (s, 3H, SiMe′ of meso-compound), −0.252 (s, 6H, SiMe2 of rac-compound).
- 13C{1H} NMR (CDCl3): δ 147.01, 146.97, 144.75, 144.70, 144.0, 143.9, 137.5*, 136.28*, 136.23*, 132.9, 132.8, 127.93*, 127.89*, 126.0*, 123.0, 122.9, 121.6*, 47.63, 47.61, 21.1*, 20.5*, 18.0, 17.8, −6.3, −6.8* (* two resonance of rac- and meso-isomers).
-
- In the Glove Box, to a solution of 2.43 g (4.4 mmol) of 1c in 100 ml of ether, 3.5 ml of 2.5M nBuLi (8.8 mmol) in hexanes was added at ambient temperature. This mixture was stirred for 24 hours and, then, cooled to −78° C.; 1.66 g (4.4 mmol) of ZrCl4(THF)2 was added. The resulting mixture was stirred for 24 hours at room temperature and, then, evaporated to dryness. To the residue 100 ml of toluene was added. This mixture was stirred for 8 hours at 90° C. The hot solution was filtered through a glass frit (G4). The residue was additionally washed with 3×50 ml of hot toluene. The filtrate was evaporated to dryness. The solid obtained was recrystallized from dichloromethane. Yield 0.78 g (25%) of red crystalline solid.
- Anal. calc. for C40H42Cl2SiZr: C, 67.38; H, 5.94. Found: C, 67.45; H, 6.00.
- 1H NMR (CD2Cl2): δ 7.63 (dt, J=8.6 Hz, J=0.9 Hz, 2H, 7,7′-H of indenyl), 7.10 (dd, J=6.9 Hz, J=0.9 Hz, 2H, 5,5′-H of indenyl), 7.02 (dd, J=8.6 Hz, J=6.9 Hz, 2H, 6,6′-H of indenyl), 6.89 (s, 2H, 3,3′-H of mesityl), 6.80 (s, 2H, 5,5′-H of mesityl), 6.35 (s, 2H, 3,3′-H of indenyl), 2.32 (s, 6H, 2,2′-Me of mesityl), 2.29 (s, 6H, 4,4′-Me of mesityl), 2.25 (s, 6H, 6,6′-Me of mesityl), 1.52 (s, 6H, 2,2′-Me), 1.28 (s, 6H, SiMe2).
- 13C{1H} NMR (CD2Cl2): δ 139.3, 138.6, 138.5, 138.2, 137.5, 137.4, 137.1, 128.4, 72.5, 23.0, 22.2, 21.6, 20.2, 3.7.
-
- In an argon atmosphere, to a solution of 28.0 ml of 15 mL of THF with 0.5 M ZnCl2 (14.0 mmol) in THF, 12.3 ml of 1.02 M 3-trifluoromethylphenylmagnesium bromide (12.6 mmol) in THF was added at ambient temperature. This mixture was stirred for 1 hour, and, then, 9.66 ml of 0.02 M Pd(PtBu3)2 (0.19 mmol, 4 mol. %) in THF and 2.42 g (4.83 mmol) of 1 were added. The resulting mixture was stirred for 5 hours at reflux. The product was isolated by flash chromatography on Silica Gel 60 (40-63 μm, d 30 mm, l 100 mm; eluent: hexanes). Yield 2.86 g (98%) of white solid of ca. 1 to 1 mixture of rac- and meso-compounds.
- Anal. calc. for C36H30F6Si: C, 71.50; H, 5.00. Found: C, 71.69; H, 5.13.
- 1H NMR (CDCl3): δ 7.39-7.84 (m, 24H, 5,5′,7,7′-H in indenyl and CF3C6H4 of rac- and meso-compound), 7.29 (m, 2H, 6,6′-H in indenyl of rac-compound), 7.23 (t, J=7.5 Hz, 2H, 6,6′-H in indenyl of meso-compound), 6.76 (s, 4H, 3,3′-H in indenyl of rac- and meso-compounds), 3.85 (s, 2H, 1,1′-H in indenyl of rac-compound), 3.82 (s, 2H, 1,1′-H in indenyl of meso-compound), 2.28 (s, 12H, 2,6-Me in mesityl of meso-compound), 2.23 (d, J=0.9 Hz, 6H, 2,2′-Me in indenyl of rac-compound), −0.11 (s, 3H, SiMe of meso-compound), −0.15 (s, 3H, SiMe′ of meso-compound), −0.16 (s, 6H, SiMe2 of rac-compound).
- 13C{1H} NMR (CDCl3): δ 148.60, 148.55, 145.7*, 142.95, 142.88, 142.12, 142.10, 132.63, 132.57, 132.2*, 130.9* (q, 1J(13C—19F)=32.2 Hz), 128.8*, 125.65, 125.62, 125.57, 125.53, 125.37, 125.34, 123.50, 123.47, 123.43, 122.9, 122.78, 122.75, 47.80, 47.74, 18.0*, −5.33, −5.39, −5.6 (* two resonance of rac- and meso-isomers).
-
- In the Glove Box, to a solution of 2.73 g (4.5 mmol) of Id in 100 ml of ether, 3.6 ml of 2.5M nBuLi (9.0 mmol) in hexanes was added at ambient temperature. This mixture was stirred for 24 hours and, then, cooled to −78° C.; 1.70 g (4.5 mmol) of ZrCl4(THF)2 was added. The resulting mixture was stirred for 24 hours at room temperature and, then, evaporated to dryness. To the residue 100 ml of toluene was added. This mixture was stirred for 8 hours at 90° C. The hot solution was filtered through a glass frit (G4). The residue was additionally washed with 3×50 ml of hot toluene. The filtrate was evaporated to dryness. The solid obtained was recrystallized from dichloromethane. Yield 0.76 g (22%) of orange crystalline solid.
- Anal. calc. for C36H28Cl2F6SiZr: C, 56.53; H, 3.69. Found: C, 56.70; H, 3.75.
- 1H NMR (CD2Cl2): δ 7.81-7.90 (m, 4H, 2,2′,6,6′-H of C6H4), 7.69-7.74 (m, 2H, 7,7′-H of indenyl), 7.51-7.63 (m, 4H, 5,5′,4,4′-H of C6H4), 7.37 (dd, J=7.0 Hz, J=0.6 Hz, 2H, 5,5′-H of indenyl), 7.12 (dd, J=8.7 Hz, J=7.0 Hz, 2H, 6,6′-H of indenyl), 6.84 (s, 2H, 3,3′-H of indenyl), 2.22 (s, 6H, 2,2′-Me of indenyl), 1.33 (s, 6H, SiMe2).
-
- In an argon atmosphere, to a solution of 29.0 ml of 0.5 M ZnCl2 (14.5 mmol) in THF, 26.0 ml of 0.5 M N,N-dimethylaminophenylmagnesium bromide (13.0 mmol) in THF was added at ambient temperature. This mixture was stirred for 1 hour, and, then, 10.0 ml of 0.02 M Pd(PtBu3)2 (0.20 mmol, 4 mol. %) in THF and 2.51 g (5.0 mmol) of 1 were added. The resulting mixture was stirred for 5 hours at reflux. The product was isolated by flash chromatography on Silica Gel 60 (40-63 μm, d 30 mm, l 100 mm; eluent: hexanes). Yield 2.55 g (92%) of white solid of ca. 1 to 1 mixture of rac- and meso-compounds.
- Anal. calc. for C38H42N2Si: C, 82.26; H, 7.63. Found: C, 82.41; H, 7.58.
- 1H NMR (CDCl3): δ 7.45-7.51 (m, 6H, 7,7′-H in indenyl of rac-compound and 3,3′,5,5′-H in C6H4 of rac- and meso-compounds), 7.34 (d, J=7.5 Hz, 2H, 7,7′-H in indenyl of meso-compound), 7.29 (m, 2H, 6,6′-H in indenyl of rac-compound), 7.26 (m, 2H, 6,6′-H in indenyl of meso-compound), 7.18 (dd, J=7.5 Hz, J=5.9 Hz, 2H, 6,6′-H in indenyl of meso-compound), 7.16(dd, J=7.5 Hz, J=5.9 Hz, 2H, 6,6′-H in indenyl of rac-compound), 6.85-6.90 (m, 12H, 3,3′-H in indenyl and 2,2′,6,6′-H in C6H4 of rac- and meso-compounds), 3.82 (s, 4H, 1,1′-H in indenyl rac- and meso-compounds), 3.04 (s, 12H, 4,4′-NMe2 of rac-compound), 3.03 (s, 12H, 4,4′-NMe2 of meso-compound), 2.27 (d, J=0.9 Hz, 6H, 2,2′-Me in indenyl of meso-compound), 2.18 (d, J=0.9 Hz, 6H, 2,2′-Me in indenyl of rac-compound), −0.16 (s, 6H, SiMe2 in rac-compound), −0.17 (s, 3H, SiMe in meso-compound), −0.19 (and SiMe′ in meso-compound).
- 13C{1H} NMR (CDCl3): δ 149.5*, 147.1, 146.9, 145.51, 145.46, 142.84, 142.76, 134.3*, 129.8*, 129.6*, 126.35, 126.30, 125.18, 125.14, 123.02, 122.97, 121.38, 121.32, 112.6*, 47.6, 47.5, 40.7*, 17.94, 17.85, −5.67 (three resonances) (* two resonance of rac- and meso-isomers).
-
- In the Glove Box, to a solution of 2.33 g (4.2 mmol) of 1e in 100 ml of ether, 3.4 ml of 2.5M nBuLi (8.4 mmol) in hexanes was added at ambient temperature. This mixture was stirred for 24 hours and, then, cooled to −78° C.; 1.58 g (4.2 mmol) of ZrCl4(THF)2 was added. The resulting mixture was stirred for 24 hours at room temperature and, then, evaporated to dryness. To the residue 100 ml of toluene was added. This mixture was stirred for 8 hours at 90° C. The hot solution was filtered through a glass frit (G4). The residue was additionally washed with 3×50 ml of hot toluene. The filtrate was evaporated to dryness. The solid obtained was recrystallized from dichloromethane. Yield 0.69 g (23%) of orange crystalline solid.
- Anal. calc. for C38H40Cl2N2SiZr: C, 63.84; H, 5.64. Found: C, 64.05; H, 5.77.
- 1H NMR (CD2Cl2): δ 7.54-7.70 (m, 6H, 7,7′-H in indenyl and 2,2′,6,6′-H in C6H4), 7.27-7.40 (m, 6H, 5,5′-H in indenyl and 3,3′,5,5′-H in C6H4), 7.09 (dd, J=8.7 Hz, J=7.2 Hz, 2H, 6,6′-H in indenyl), 6.87 (s, 2H, 3,3′-H in indenyl), 3.15 (s, 12H, 4,4′-NMe2 in C6H4), 2.20 (s, 6H, 2,2′-Me in indenyl), 1.32 (s, 6H, SiMe2).
-
- In an argon atmosphere, to a solution of 1.74 g (13.0 mmol) of benzothiophene in 30 ml of THF, 5.24 ml of 2.5 M nBuLi (13.0 mmol) in hexanes was added at ambient temperature. This mixture was stirred for 2 hours, and, then, 29.0 ml of 0.5 M ZnCl2 (14.5 mmol) in THF was added. The resulting mixture was stirred for 1 hour. Then, 10.0 ml of 0.02 M Pd(PtBu3)2 (0.20 mmol, 4 mol. %) in THF and 2.37 g (5.0 mmol) of 1 were added. This mixture was stirred for 5 hours at reflux. The product was isolated by flash chromatography on Silica Gel 60 (40-63 μm, d 30 mm, l 100 mm; eluent: hexanes). Yield 2.76 g (95%) of white solid of ca. 1 to 1 mixture of rac- and meso-compounds.
- Anal. calc. for C38H32S2Si: C, 78.57; H, 5.55. Found: C, 78.70; H, 5.46.
- 1H NMR (CDCl3): δ 6.96-7.82 (m, 36H, 3,3′,5,5′,6,6′,7,7′-H in indenyls and benzothienyls of rac- and meso-compounds), 3.70 (s, 2H, 1,1′-H in indenyls of rac- or meso-compound), 3.66 (s, 2H, 1,1′-H in indenyls of meso- or rac-compound), 2.22 (m, 6H, 2,2′-Me in indenyls of rac- or meso-compound), 2.07 (m, 6H, 2,2′-Me in indenyls of meso- or rac-compound), −0.11 (s, 3H, SiMe2 of rac-compound), −0.14 (s, 3H, SiMe of meso-compound), −0.18 (s, 6H, SiMe′ of meso-compound).
- 13C{1H} NMR (CDCl3): δ 148.7, 148.5, 145.8*, 143.83, 143.81, 143.0, 142.8, 140.5*, 139.77, 149.76, 126.57, 126.55, 126.2, 126.1, 126.0, 125.9, 124.3*, 123.9*, 123.39, 123.35, 123.07, 123.04, 122.9, 122.05, 122.03, 121.5, 47.8, 47.7, 18.0, 17.8, −4.9, −5.1, −5.2 (* two resonance of rac- and meso-isomers).
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- In the Glove Box, to a solution of 2.50 g (4.3 mmol) of 1f in 100 ml of ether, 3.45 ml of 2.5M nBuLi (8.6 mmol) in hexanes was added at ambient temperature. This mixture was stirred for 24 hours and, then, cooled to −78° C.; 1.62 g (4.3 mmol) of ZrCl4(THF)2 was added. The resulting mixture was stirred for 24 hours at room temperature and, then, evaporated to dryness. To the residue 100 ml of toluene was added. This mixture was stirred for 8 hours at 90° C. The hot solution was filtered through a glass frit (G4). The residue was additionally washed with 5×70 ml of hot toluene. The filtrate was evaporated to dryness. The solid obtained was recrystallized from dichloromethane. Yield 1.12 g (35%) of orange crystalline solid.
- Anal. calc. for C38H30Cl2S2SiZr: C, 61.59; H, 4.08. Found: C, 61.74; H, 4.17.
- 1H NMR (CD2Cl2): δ 7.77 (m, 4H, 4,4′,7,7′-H of benzothienyl), 7.71 (d, J=8.7 Hz, 2H, 7,7′-H of indenyl), 7.60 (s, 2H, 3,3′-H of benzothienyl), 7.57 (d, J=7.1 Hz, 2H, 5,5′-H of indenyl), 7.29 (m, 4H, 5,5′,6,6′-H of benzothienyl), 7.21 (s, 2H, 3,3′-H of indenyl), 7.11 (dd, J=8.7 Hz, J=7.1 Hz, 2H, 6,6′-H of indenyl), 2.26 (s, 6H, 2,2′-Me of indenyl), 1.34 (s, 6H, SiMe2).
- 13C{1H} NMR (CD2Cl2): δ 144.7, 138.3, 138.1, 137.6, 135.6, 133.3, 130.2, 130.1, 128.3, 128.1 (two resonances), 127.4 (three resonances), 121.8, 120.6, 72.4, 20.7, 0.7.
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- In an argon atmosphere, to a solution of 50 mL of THF with 58.0 ml of 0.5 M ZnCl2 (29.0 mmol) in THF, 8.7 ml of 3.0 M methylmagnesium chloride (26.0 mmol) in THF was added at ambient temperature. This mixture was stirred for 1 hour, and, then, 20.0 ml of 0.02 M Pd(PtBu3)2 (0.40 mmol, 4 mol. %) in THF and 5.02 g (10.0 mmol) of 1 were added. The resulting mixture was stirred for 5 hours at reflux. The product was isolated by flash chromatography on Silica Gel 60 (40-63 μm, d 50 mm, l 100 mm; eluent: hexanes). Yield 3.34 g (97%) of white solid of ca. 1 to 1 mixture of rac- and meso-compounds.
- Anal. calc. for C24H28Si: C, 83.66; H, 8.19. Found: C, 83.70; H, 8.26.
- 1H NMR (CDCl3): δ 7.32-7.38 (m, 4H, 7,7′-H in rac- and meso-compounds), 7.19-7.25 (m, 4H, 5,5′-H in rac- and meso-compounds), 6.96-7.06 (m, 4H, 6,6′-H in rac- and meso-compounds), 6.71 (m, 4H, 3,3′-H in rac- and meso-compounds), 3.75 (s, 2H, 1,1′-H in rac-compound), 3.72 (s, 2H, 1,1′-H in meso-compound), 2.45 (s, 6H, 4,4′-Me in rac-compound), 2.44 (s, 6H, 4,4′-Me in meso-compound), 2.26 (d, J=1.0 Hz, 6H, 2,2′-Me in rac-compound), 2.21 (d, J=1.0 Hz, 6H, 2,2′-Me in meso-compound), −0.28 (s, 3H, SiMe in meso-compound), −0.325 (s, 6H, SiMe2 in rac-compound), −0.334 (s, 3H, SiMe′ in meso-compound).
- 13C{1H} NMR (CD2Cl2): δ 146.6, 146.5, 144.61, 144.55, 144.26, 144.20, 129.04, 129.01, 126.0 (two resonances), 124.98, 124.95, 122.81, 122.74, 120.71, 120.67, 47.49, 47.42, 18.8 (two resonances), 18.0 (two resonances), −5.7, −5.9, −6.1.
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- In the Glove Box, to a solution of 3.04 g (5.3 mmol) of 1 g in 100 ml of ether, 4.25 ml of 2.5M nBuLi (10.6 mmol) in hexanes was added at ambient temperature. This mixture was stirred for 24 hours and, then, cooled to −78° C.; 2.00 g (5.3 mmol) of ZrCl4(THF)2 was added. The resulting mixture was stirred for 24 hours at room temperature and, then, evaporated to dryness. To the residue 100 ml of toluene was added. This mixture was stirred for 8 hours at 90° C. The hot solution was filtered through a glass frit (G4). The residue was additionally washed with 3×50 ml of hot toluene. The filtrate was evaporated to dryness. The solid obtained was recrystallized from dichloromethane. Yield 0.80 g (30%) of yellow crystalline solid.
- Anal. calc. for C24H26Cl2SiZr: C, 57.12; H, 5.19. Found: C, 57.22; H, 5.24.
- 1H NMR (CD2Cl2): δ 7.35-7.41 (m, 2H, 7,7′-H), 6.99-7.04 (m, 2H, 5,5′-H), 6.80-6.87 (m, 2H, 6,6′-H), 6.73 (s, 2H, 3,3′-H), 2.31 (s, 6H, 4,4′-Me), 2.11 (s, 6H, 2,2′-Me), 0.92 (s, 6H, SiMe2).
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- In an argon atmosphere, to a solution of 15 mL of THF with 29.0 ml of 0.5 M ZnCl2 (14.5 mmol) in THF, 13.0 ml of 1.0 M 2-(trifluoromethyl)phenyl magnesium bromide (13.0 mmol) in THF was added at ambient temperature. This mixture was stirred for 1 hour, and, then, 10.0 ml of 0.02 M Pd(PtBu3)2 (0.20 mmol, 4 mol. %) in THF and 2.37 g (5.0 mmol) of 1 were added. The resulting mixture was stirred for 5 hours at reflux. The product was isolated by flash chromatography on Silica Gel 60 (40-63 μm, d 30 mm, l 100 mm; eluent: hexanes). Yield 2.93 g (97%) of white solid of ca. 1 to 1 mixture of rac- and meso-compounds.
- Anal. calc. for C36H30F6Si: C, 71.50; H, 5.00. Found: C, 71.66; H, 5.12.
- 1H NMR (CDCl3): δ 7.21-7.94 (m, 28H, 5,5′,6,6′,7,7′-H in indenyl and 3,3′,4,4′,5,5′,6,6′-H in C6H4 of rac- and meso-isomers), 6.40 (m, 4H, 3,3′-H in indenyl of rac- and meso-isomers), 3.92-4.07 (m, 4H, 1,1′-H in indenyl of rac- and meso-isomers), 2.21-2.39 (m, 12H, 2,2′-Me in indenyl of rac- and meso-isomers), −0.04-0.24 (m, 12H, Me2Si in indenyl of rac- and meso-isomers).
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- To a solution of 4.84 g (8.0 mmol) of 1i in 150 ml of ether, 6.50 ml 2.5 M (16.3 mmol) of nBuLi in hexanes was added dropwise over 15 min at 0° C. This mixture was stirred for 5 h at room temperature and then cooled to −78° C. Next, 3.02 g (8.0 mmol) of ZrCl4(THF)2 was added. The resulting mixture was slowly (ca. 2 h) warmed to ambient temperature with vigorous stirring and then stirred for 24 h. The organic solvents were distilled off under reduced pressure, and 200 ml of toluene was added. This mixture was stirred for 1 h at 80° C. and then filtered through a glass frit (G4) at this temperature. The filtrate was evaporated to ca. 80 ml. The orange crystals precipitated at −30° C. were collected, washed with 2×5 ml of cold toluene and 3×30 ml of hexanes, and dried in vacuum. This procedure gave 1.71 g (28%) of pure rac-1i@.
- Anal. calc. for C36H28Cl2F6SiZr: C, 56.53; H, 3.69. Found: C, 56.60; H, 3.77.
- 1H NMR (CD2Cl2): δ 7.85 (m, 2H, 6,6′-H in C6H4), 7.77 (m, 2H, 3,3′-H in C6H4), 7.73 (m, 5,5′-H in indenyl), 7.65 (m, 4,4′-H in C6H4), 7.53 (m, 5,5′-H in C6H4), 7.26 (m, 7,7′-H in indenyl), 7.09 (dd, J=8.8 Hz, J=7.0 Hz, 2H, 6,6′-H in indenyl), 6.41 (s, 2H, 3,3′-H in indenyl), 2.23 (s, 6H, 2,2′-Me in indenyl), 1.34 (s, 6H, SiMe2).
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- In an argon atmosphere, to a solution of 15 mL of THF with 29.0 ml of 0.5 M ZnCl2 (14.5 mmol) in THF, 13.0 ml of 1.0 M 4-(tert-butyl) phenylmagnesium bromide (13.0 mmol) in THF was added at ambient temperature. This mixture was stirred for 1 hour, and, then, 10.0 ml of 0.02 M Pd(PtBu3)2 (0.20 mmol, 4 mol. %) in THF and 2.37 g (5.0 mmol) of 1 were added. The resulting mixture was stirred for 5 hours at reflux. The product was isolated by flash chromatography on Silica Gel 60 (40-63 μm, d 30 mm, l 100 mm; eluent: hexanes). Yield 2.85 g (98%) of white solid of ca. 1 to 1 mixture of rac- and meso-compounds.
- Anal. calc. for C42H48Si: C, 86.84; H, 8.33. Found: C, 86.90; H, 8.39.
- 1H NMR (CDCl3): δ 7.52-7.57 (m, 18H, 7,7′-H in indenyl of rac- or meso-isomers and 2,2′,3,3′,5,5′,6,6′-H in C6H4 of rac- and meso-isomers), 7.39-7.43 (m, 2H, 7,7′-H in indenyl of meso- or rac-isomers), 7.31-7.36 (m, 4H, 5,5′-H in indenyl of rac- and meso-isomers), 7.19-7.26 (m, 4H, 6,6′-H in indenyl of rac- and meso-isomers), 6.92 (m, 4H, 3,3′-H in indenyl of rac- and meso-isomers), 3.88 (m, 2H, 1,1′-H in indenyl of rac- or meso-isomer), 3.85 (m, 2H, 1,1′-H in indenyl of meso- or rac-isomer), 2.30 (m, 6H, 2,2′-Me in indenyl of rac- or meso-isomer), 2.24 (m, 6H, 2,2′-Me in indenyl of meso- or rac-isomer), 1.46 (s, 18H, tBu of rac- or meso-isomer), 1.45 (s, 18H, tBu of meso- or rac-isomer), −0.13 (s, 3H, MeMe′Si of meso-isomer), −0.15 (s, 3H, MeMe′Si of meso-isomer), −0.16 (s, 6H, Me2Si of rac-isomer). 13C{1H} NMR (CDCl3): δ 149.6, 147.5, 147.4, 145.52, 145.50, 143.00, 142.95, 138.49, 138.45, 134.09, 134.04, 128.6, 126.3, 126.2, 125.63, 125.58, 125.3, 123.14, 123.06, 122.05, 122.00, 47.7, 47.6, 34.6, 31.5, 18.03, 18.01, −5.58, −5.59, −5.8.
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- To a solution of 2.91 g (5.0 mmol) of 1k in 100 ml of ether, 4.10 ml 2.5 M (10.3 mmol) of n BuLi in hexanes was added dropwise over 15 min at 0° C. This mixture was stirred for 12 h at room temperature and then cooled to −78° C. Next, 1.89 g (5.0 mmol) of ZrCl4(THF)2 was added. The resulting mixture was slowly (ca. 1.5 h) warmed to ambient temperature with vigorous stirring and then stirred for 12 h. The organic solvents were distilled off under reduced pressure, and 100 ml of toluene was added. This mixture was stirred for 1 h at 80° C. and then filtered through a glass frit (G4) at this temperature. The filtrate was evaporated to ca. 30 ml. The yellow crystals precipitated at −30° C. were collected, washed with 2×5 ml of cold toluene and 3×30 ml of hexanes, and dried in vacuum. This procedure gave 0.67 g (18%) of pure rac-1k@.
- Anal. calc. for C42H46Cl2SiZr: C, 68.07; H, 6.26. Found: C, 68.22; H, 6.05.
- 1H NMR (CD2Cl2): δ 7.64 (m, 2H, 7,7′-H of indenyl), 7.50-7.56 (m, 4H, 2,2′,6,6′-H of C6H4), 7.41-7.47 (m, 4H, 3,3′,5,5′-H of C6H4) 7.33 (dd, J=7.0 Hz, J=0.8 Hz, 2H, 5,5′-H of indenyl), 7.08 (dd, J=8.7 Hz, J=7.0 Hz, 2H, 6,6′-H of indenyl), 6.91 (m, 2H, 3,3′-H of indenyl), 2.21 (d, J=0.4 Hz, 6H, 2,2′-Me of indenyl), 1.31 (s, 6H, SiMe2), 1.30 (s, 18H, tBu).
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- In a three-necked round-bottom 500 ml flask equipped with a reflux condenser, dropping funnel with pressure-equalizing, and magnetic stirring bar 5.95 g (0.26 mol) of sodium metal were dissolved in 200 ml of dry ethanol. To the resulting solution 45.1 g (0.26 mol) of diethylmethylmalonate were added dropwise within 15 min. This mixture was stirred for 15 min; then, 62.1 g (0.24 mol) of 2-bromo-1-(bromomethyl)-3-methylbenzene in 50 ml of ethanol were added, while vigorously stirring, at a rate that allowed the reaction mixture to maintain a gentle reflux. This mixture was further refluxed for 4 h and cooled to room temperature. A solution of 51.8 g of KOH in 150 ml of water was added. This mixture was refluxed for 3 h to saponificate the ester formed. Ethanol and water were distilled off. To the residue 200 ml of water and, then, 12 M HCl (to pH 1) were added. The substituted methylmalonic acid precipitate was separated, washed with 2×60 ml of cold water, and dried overnight on a watch glass. Crude 3-(2-bromo-3-methylphenyl)-2-methylpropanoic acid was obtained after decarboxilation of this substituted methylmalonic acid by heating it at 160° C. for 2 hours. The product was used without further purification. Mixture of this acid and 60 ml of SOCl2 was stirred for 24 h at ambient temperature. Thionyl chloride was distilled off. The crude 3-(2-bromo-3-methylphenyl)-2-methylpropanoyl chloride was dissolved in 200 ml of CH2Cl2 and was added dropwise, while vigorously stirring, to a suspension of 37.7 g (0.28 mol) of AlCl3 in 800 ml of CH2Cl2 over a period of 1 h at 0° C. Then, this mixture was refluxed for 3 h, cooled to ambient temperature, and poured over 300 cm3 of ice. The organic layer was separated. The aqueous layer was extracted with 3×100 ml of methyl-tert-butyl ether. The combined organic fractions were dried over K2CO3 and evaporated to dryness. Fractional distillation gave the title indanone, b.p. 120-121° C./1 mm Hg. Yield 47.6 g (85%) of colorless solid.
- Anal. calc. for C11H11BrO: C, 55.25; H, 4.64. Found: C, 55.35; H, 4.66.
- 1H NMR (CDCl3): δ 7.64 (d, J=7.8 Hz, 1H, 7-H), 7.22 (d, J=7.8 Hz, 1H, 6-H), 3.29 (dd, J=17.6 Hz, J=7.9 Hz, 1H, 3-H), 2.70 (m, 1H, 2-H), 2.59 (dd, J=17.6 Hz, J=3.9 Hz, 1H, 3′-H), 2.45 (s, 3H, 5-Me), 1.28 (d, J=7.6 Hz, 2-Me).
- 13C{1H} NMR (CDCl3): δ 208.1, 153.8, 145.1, 136.1, 130.3, 124.1, 122.3, 42.2, 36.5, 23.1, 16.2.
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- To a solution of 47.6 g (199 mmol) of 4-bromo-2,5-dimethyl-1-indanone in 270 ml of THF-methanol (2:1, vol.), 11.3 g (299 mmol) of NaBH4 were added for 1 h at −5° C. (Caution: temperature must be lower than 0° C.). The mixture was stirred overnight at ambient temperature, then diluted with 300 ml of water, and acidified with 10% HCl to pH=1. The crude product was extracted with 3×200 ml of CH2Cl2. This extract was evaporated to dryness. To the white solid obtained 500 ml of toluene was added. This toluene solution was treated with a catalytic amount of pTolSO3H (ca. 2 g) for 2 hours at reflux using a Dean-Stark head. The reaction was cooled to room temperature, washed with aqueous NaHCO3, dried over Na2SO4, and evaporated to dryness. The product was isolated by flash chromatography on Silica Gel 60 (40-63 μm, d 30 mm, l 300 mm; eluent: hexanes). Yield 38.7 g (87%) of white crystalline product.
- Anal. calc. for C11H11Br: C, 59.22; H, 4.97. Found: C, 59.40; H, 5.04.
- 1H NMR (CDCl3) of 4-bromo-2,5-dimethyl-1H-indene: δ 7.03 (m, 1H, 7-H in indenyl), 6.97 (d, J=7.4 Hz, 1H, 6-H on indenyl), 6.36 (m, 1H, 3-H in indenyl), 3.22 (m, 2H, CH2), 2.35 (s, 3H, 5-Me in indenyl), 2.09 (m, 3H, 2-Me in indenyl); 7-bromo-2,6-dimethyl-1H-indene: δ 7.03 (m, 1H, 4-H in indenyl), 7.00 (d, J=7.5 Hz, 1H, 5-H on indenyl), 6.40 (m, 1H, 3-H in indenyl), 3.20 (m, 2H, CH2), 2.38 (s, 3H, 6-Me in indenyl), 2.09 (m, 3H, 2-Me in indenyl).
- 13C{1H} NMR (CDCl3) of 7-bromo-2,6-dimethyl-1H-indene: δ 145.6, 144.6, 144.0, 132.5, 128.7, 126.9, 121.0, 118.3, 44.8, 22.3, 16.6.
-
- In an argon atmosphere, to a solution of 10.0 g (44.8 mmol) of a mixture of 4-bromo-2,5-dimethyl-1H- and 7-bromo-2,6-dimethyl-1H-indenes in 400 ml of diethyl ether, 17.9 ml of 2.5 M nBuLi (44.8 mmol) in hexanes was added at ambient temperature. This mixture was stirred overnight at room temperature, and, then, 2.72 ml (2.89 g, 22.4 mmol) of Me2SiCl2 was added. The resulting mixture was stirred for 24 hours at ambient temperature; then 50 ml of water was added. The organic layer was separated, dried over Na2SO4, and evaporated to dryness. The residue was washed with 3×30 ml of hexanes and dried in vacuum. Yield 7.02 g (61%) of white solid of ca. 1 to 1 mixture of rac- and meso-compounds.
- Anal. calc. for C24H26Br2Si: C, 57.38; H, 5.22. Found: C, 57.55; H, 5.34.
- 1H NMR (CDCl3): δ 7.53 (d, J=7.5 Hz, 2H, 7,7′-H in rac-compound), 7.41 (d, J=7.5 Hz, 2H, 7,7′-H in meso-compound), 7.25 (d, J=7.5 Hz, 2H, 6,6′-H in rac-compound), 7.22 (d, J=7.5 Hz, 2H, 6,6′-H in meso-compound), 7.02 (m, 4H, 3,3′-H in rac- and meso-compounds), 4.02 (s, 2H, 1,1′-H in rac-compound), 3.99 (s, 2H, 1,1′-H in meso-compound), 2.74 (s, 6H, 5,5′-Me in rac-compound), 2.72 (s, 6H, 5,5′-Me in meso-compound), 2.51 (m, 6H, 2,2′-Me in meso-compound), 2.46 (m, 6H, 2,2′-Me in rac-compound), 0.08 (s, 3H, SiMe in meso-compound), 0.015 (s, 3H, SiMe′ in meso-compound), 0.006 (s, 6H, SiMe2 in rac-compound).
-
- In an argon atmosphere, to a solution of 15 mL of THF with 29.0 ml of 0.5 M ZnCl2 (14.5 mmol) in THF, 13.0 ml of 1.0 M phenylmagnesium bromide (13.0 mmol) in THF was added at ambient temperature. This mixture was stirred for 1 hour, and, then, 10.0 ml of 0.02 M Pd(PtBu3)2 (0.20 mmol, 4 mol. %) in THF and 2.51 g (5.0 mmol) of 2 were added. The resulting mixture was stirred for 5 hours at reflux. The product was isolated by flash chromatography on Silica Gel 60 (40-63 μm, d 30 mm, l 100 mm; eluent: hexanes). Yield 2.36 g (95%) of white solid of ca. 1 to 1 mixture of rac- and meso-compounds.
- Anal. calc. for C36H36Si: C, 87.04; H, 7.30. Found: C, 87.91; H, 7.38.
- 1H NMR (CDCl3): δ 7.28-7.50 (m, 24H, 7,7′-H and 4,4′-Ph in indenyl of rac- and meso-compounds), 7.07 (d, J=7.5 Hz, 2H, 6,6′-H in indenyl of rac- or meso-compound), 7.04 (d, J=7.5 Hz, 2H, 6,6′-H in indenyl of meso- or rac-compound), 6.34 (m, 4H, 3,3′-H in rac- and meso-compounds), 3.80 (s, 2H, 1,1′-H in indenyl of rac- or meso-compound), 3.79 (s, 2H, 1,1′-H in indenyl of meso- or rac-compound), 2.254 (s, 6H, 5,5′-Me in indenyl of rac- or meso-compound), 2.246 (s, 6H, 5,5′-Me in indenyl of meso- or rac-compound), 2.21 (d, J=0.9 Hz, 6H, 2,2′-Me in indenyl of rac- or meso-compound), 2.14 (d, J=0.9 Hz, 6H, 2,2′-Me in indenyl of meso- or rac-compound), −0.21 (s, 3H, SiMe of meso-compound), −0.22 (s, 9H, SiMe′ of meso-compound and SiMe2 of rac-compound).
- 13C{1H} NMR (CDCl3): δ 147.17, 147.05, 144.58, 144.53, 142.27, 142.23, 140.4 (two resonances), 133.89, 133.84, 132.05, 132.01, 129.9 (br), 129.7 (br), 128.0 (two resonances), 126.6 (two resonances), 126.38, 126.33, 124.88, 124.81, 122.04, 122.01, 47.32, 47.26, 20.1 (two resonances), 17.89, 17.85, −5.9, −6.0, −6.1.
-
- In the Glove Box, to a solution of 2.18 g (4.4 mmol) of 2a in 100 ml of ether, 3.5 ml of 2.5M nBuLi (8.8 mmol) in hexanes was added at ambient temperature. This mixture was stirred for 24 hours and, then, cooled to −78° C.; 1.66 g (4.4 mmol) of ZrCl4(THF)2 was added. The resulting mixture was stirred for 24 hours at room temperature and, then, evaporated to dryness. To the residue 100 ml of toluene was added. This mixture was stirred for 8 hours at 90° C. The hot solution was filtered through a glass frit (G4). The residue was additionally washed with 3×50 ml of hot toluene. The filtrate was evaporated to dryness. The solid obtained was recrystallized from dichloromethane. Yield 0.84 g (29%) of orange crystalline solid.
- Anal. calc. for C36H34Cl2SiZr: C, 65.83; H, 5.22. Found: C, 65.95; H, 5.31.
- 1H NMR (CD2Cl2): δ 7.51 (d, J=8.9 Hz, 2H, 7,7′-H in indenyl), 7.40 (m, 4H, 2,2′,6,6′-H in Ph), 7.35 (m, 4H, 3,3′,5,5′-H in Ph), 7.20 (m, 2H, 4,4′-H in Ph), 6.95 (d, J=8.9 Hz, 2H, 6,6′-H in indenyl), 6.35 (m, 2H, 3,3′-H in indenyl), 2.23 (s, 6H, 5,5′-Me), 2.14 (s, 6H, 2,2′-Me), 1.26 (s, 6H, SiMe2).
-
- In an argon atmosphere, to a solution of 15 mL of THF with 29.0 ml of 0.5 M ZnCl2 (14.5 mmol) in THF, 13.0 ml of 1.0 M 3,5-bis(trifluoromethyl) phenylmagnesium bromide (13.0 mmol) in THF was added at ambient temperature. This mixture was stirred for 1 hour, and, then, 10.0 ml of 0.02 M Pd(PtBu3)2 (0.20 mmol, 4 mol. %) in THF and 2.51 g (5.0 mmol) of 2 were added. The resulting mixture was stirred for 5 hours at reflux. The product was isolated by flash chromatography on Silica Gel 60 (40-63 μm, d 30 mm, l 100 mm; eluent: hexanes). Yield 3.65 g (95%) of white solid of ca. 1 to 1 mixture of rac- and meso-compounds.
- Anal. calc. for C40H32F12Si: C, 62.49; H, 4.20. Found: C, 62.55; H, 4.28.
- 1H NMR (CDCl3): δ 8.02 (m, 4H, 4,4′-H in aryl of rac- and meso-isomers), 7.93 (m, 4H, 2,2′,6,6′-H in aryl of rac- or meso-isomer), 7.89 (m, 4H, 2,2′,6,6′-H in aryl of meso- or rac-isomer), 7.57 (m, 2H, 7,7′-H in indenyl of rac- or meso-isomer), 7.46 (m, 2H, 7,7′-H in indenyl of meso- or rac-isomer), 7.20 (m, 2H, 6,6′-H in indenyl of rac- or meso-isomer), 7.17 (m, 2H, 6,6′-H in indenyl of meso- or rac-isomer), 6.36 (m, 4H, 3,3′-H in indenyl of rac- and meso-isomers), 3.92 (m, 2H, 1,1′-H in indenyl of rac- or meso-isomer), 3.91 (m, 2H, 1,1′-H in indenyl of meso- or rac-isomer), 2.34 (m, 6H, 2,2′-Me of rac- or meso-isomer), 2.33 (s, 6H, 5,5′-Me of rac- or meso-isomer), 2.32 (s, 6H, 5,5′-Me of meso- or rac-isomer), 2.28 (m, 6H, 2,2′-Me of meso- or rac-isomer), −0.05 (s, 3H, SiMeMe′ of meso-isomer), −0.08 (s, 3H, SiMeMe′ of meso-isomer), −0.09 (s, 6H, SiMe2 of rac-isomer).
-
- To a solution of 6.15 g (8.0 mmol) of 2b in 100 ml of ether, 6.50 ml 2.5 M (16.3 mmol) of nBuLi in hexanes was added dropwise over 15 min at 0° C. This mixture was stirred for 12 h at room temperature and then cooled to −78° C. Next, 3.02 g (8.0 mmol) of ZrCl4(THF)2 was added. The resulting mixture was slowly (ca. 1.5 h) warmed to ambient temperature with vigorous stirring and then stirred for 20 h. The organic solvents were distilled off under reduced pressure, and 100 ml of dichloromethane was added. This mixture was filtered through a glass frit (G4). The precipitate was washed by 4×20 ml of dichloromethane and dried in vacuum. This procedure gave 1.41 g (19%) of pure rac-2b@ as orange-red powder.
- Anal. calc. for C40H30Cl2F12SiZr: C, 51.72; H, 3.26. Found: C, 51.60; H, 3.14.
- 1H NMR (CD2Cl2): δ 7.47-7.57 (m, 6H, 2,2′,4,4′,6,6′-H in aryl), 6.95-6.99 (m, 4H, 6,6′,7,7′-H in indenyl), 6.43 (s, 2H, 3,3′-H in indenyl), 2.29 (s, 6H, 5,5′-Me in indenyl), 2.19 (s, 6H, 2,2′-Me in indenyl), 1.29 (s, 6H, SiMe2).
-
- To a suspension of 250 g (1.89 mol) of AlCl3 (anhydrous powder) in 350 ml of CHCl3, 129 g (0.85 mol) of 5-methyl-4,5-dihydro-6H-cyclopenta[b]thiophen-6-one in 130 ml of CHCl3 was added at 0° C. over a period of 0.5 hours. The reaction mixture was stirred for 10 min at this temperature; then a solution of 46.7 ml of Br2 (0.91 mol) in 90 ml of CHCl3 was added dropwise over a period of 1 hour. The resulting mixture was stirred for 1 hour at room temperature and, then, poured over 2000 cm3 of ice. The organic layer was separated. The aqueous layer was extracted with 4×200 ml of CH2Cl2. The combined organic fractions were washed with 1000 ml of the saturated aqueous Na2CO3, dried over K2CO3, passed through short column with Silica Gel 60 (40-63 μm, d 40 mm, l 50 mm), and evaporated to dryness. Fractional distillation gave white crystalline product, b.p. 128° C./0.8 mm Hg. Yield 185 g (94%).
- Anal. calc. for C8H7BrOS: C, 41.58; H, 3.05. Found: C, 41.78; H, 3.16.
- 1H NMR (CDCl3): δ 7.77 (s, 1H, 2-H), 3.15 (dd, J=17.2 Hz, J=7.0 Hz, 1H, 4-H), 3.04 (m, 1H, 5-H), 2.50 (dd, J=17.2 Hz, J=2.9 Hz, 1H, 4′-H), 1.34 (d, J=7.5 Hz, 3H, 5-Me).
- 13C{1H} NMR (CDCl3): δ 199.3, 165.6, 140.2, 136.7, 108.4, 47.4, 32.3, 16.7.
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- To a solution of 5.0 g (21.5 mmol) of 3-bromo-5-methyl-4,5-dihydro-6H-cyclopenta[b]thiophen-6-one in 60 ml of THF-methanol (2:1, vol.), 1.30 g (34.4 mmol) of NaBH4 was added over a period of 1 hour at −5° C. (Caution: temperature must be lower than 0° C.). The mixture was stirred for 10 hours at ambient temperature, then diluted with 20 ml of water, and acidified with 10% HCl to pH=1. The crude product was extracted with 3×100 ml of CH2Cl2. This extract was washed with the saturated aqueous Na2CO3, dried over K2CO3, and evaporated to dryness. To the yellow oil obtained, 150 ml of toluene was added. This toluene solution was treated with a catalytic amount of pTolSO3H (ca. 0.2 g) for 10 min at reflux, cooled to room temperature, and, then, passed through a short Silica Gel 60 column (40-63 μm, d 20 mm, 150 mm). This column was additionally eluted with 300 ml of hexanes-methyl-tert-butyl ether mixture (10:1, vol.). The chromatographed product was evaporated to dryness. This procedure gave 4.61 g (99%) of beige crystalline product of 3-bromo-5-methyl-4H-cyclopenta[b]thiophene (containing 3-5% of 3-bromo-5-methyl-6H-cyclopenta[b]thiophene).
- Anal. calc. for C8H7BrS: C, 44.67; H, 3.28. Found: C, 44.80; H, 3.34.
- 1H NMR (CDCl3): δ 6.94 (s, 1H, 2-H), 6.43 (m, 1H, 6-H), 3.10 (d, J=1.3 Hz, 2H, CH2), 2.16 (d, J=1.5 Hz, 3H, Me).
- 13C{1H} NMR (CDCl3): δ 129.0, 127.6, 127.5, 122.6, 120.2, 106.5, 40.0, 17.4.
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- In an argon atmosphere, to a solution of 5.50 g (25.6 mmol) of 3-bromo-5-methyl-4H-cyclopenta[b]thiophene in 250 ml of diethyl ether, 16.0 ml of 1.6 M MeLi (25.6 mmol) in ether was added at −60° C. This mixture was stirred for 1 hour at room temperature and, then, cooled to 0° C. To this mixture, 1.55 ml (12.8 mmol) of Me2SiCl2 was added at this temperature. The resulting mixture was stirred for 12 hours at ambient temperature. Then, 50 ml of water was added. The organic layer was separated, dried over K2CO3, and evaporated to dryness in vacuum. The crude product was purified using flash chromatography on Silica Gel 60 (40-63 μm, d 40 mm, l 500 mm, eluent hexanes). This procedure gave 2.61 g (42%) the title product of ca. 60% purity (i.e. up to 40% of 4,4′- and 4,6′-substituted isomers). Analytically pure 3 was obtained by crystallization of crude product from hexanes-ether (3:1, vol.).
- Anal. calc. for C18H18Br2S2Si: C, 44.45; H, 3.73. Found: C, 44.90; H, 3.87.
- 1H NMR (CDCl3): rac-isomer, δ 7.11 (s, 2H, 2,2′-H), 6.52 (m, 2H, 4,4′-H), 3.84 (s, 2H, 6,6′-H), 2.25 (s, 6H, 5,5′-Me), −0.25 (s, 6H, SiMe2); meso-isomer, δ 7.09 (s, 2H, 2,2′-H), 6.52 (m, 2H, 4,4′-H), 3.76 (s, 2H, 6,6′-H), 2.26 (s, 6H, 5,5′-Me), −0.21 (s, 3H, SiMe), −0.26 (s, 3H, SiMe′).
-
- In an argon atmosphere, to a solution of 15 mL of THF with 25.4 ml of 0.5 M ZnCl2 (12.7 mmol) in THF, 11.4 ml of 1.0 M phenylmagnesium bromide (11.4 mmol) in THF was added at ambient temperature. This mixture was stirred for 1 hour, and, then, 8.8 ml of 0.02 M Pd(PtBu3)2 (0.18 mmol, 4 mol. %) in THF and 2.14 g (4.40 mmol) of 3 were added. The resulting mixture was stirred for 5 hours at reflux. The product was isolated by flash chromatography on Silica Gel 60 (40-63 μm, d 30 mm, l 100 mm; eluent: hexanes). Yield 2.03 g (96%) of white solid of ca. 1 to 2 mixture of rac- and meso-compounds.
- Anal. calc. for C30H28S2Si: C, 74.95; H, 5.87. Found: C, 75.20; H, 5.99.
- 1H NMR (CDCl3), rac-3b: δ 7.63-7.67 (m, 4H, 2,2′,6,6′-H in C6H4), 7.39-7.46 (m, 4H, 3,3′,5,5′-H in C6H4), 7.30-7.34 (m, 2H, 4,4′-H in C6H4), 7.29 (d, J=0.6 Hz, 2H, 5-H in cyclopenta[b]thienyl), 6.80 (m, 2H, 3,3′-H in cyclopenta[b]thienyl), 3.94 (m, 2H, 1,1′-H in cyclopenta[b]thienyl), 2.19 (d, J=1.4 Hz, 6H, 2,2′-Me in cyclopenta[b]thienyl), −0.23 (s, 6H, SiMe2); meso-3b: δ 7.62-7.66 (m, 4H, 2,2′,6,6′-H in C6H4), 7.39-7.46 (m, 4H, 3,3′,5,5′-H in C6H4), 7.30-7.34 (m, 2H, 4,4′-H in C6H4), 7.26 (d, J=0.6 Hz, 2H, 5-H in cyclopenta[b]thienyl), 6.81 (m, 2H, 3,3′-H in cyclopenta[b]thienyl), 3.83 (m, 2H, 1,1′-H in cyclopenta[b]thienyl), 2.32 (d, J=1.4 Hz, 6H, 2,2′-Me in cyclopenta[b]thienyl), −0.20 (s, 3H, SiMe), −0.21 (s, 3H, SiMe′).
-
- In the Glove Box, to a solution of 1.92 g (4.0 mmol) of 3a in 100 ml of ether, 3.2 ml of 2.5M nBuLi (8.0 mmol) in hexanes was added at ambient temperature. This mixture was stirred for 24 hours and, then, cooled to −78° C.; 1.51 g (4.0 mmol) of ZrCl4(THF)2 was added. The resulting mixture was stirred for 24 hours at room temperature and, then, evaporated to dryness. To the residue 100 ml of toluene was added. This mixture was stirred for 8 hours at 90° C. The hot solution was filtered through a glass frit (G4). The residue was additionally washed with 3×50 ml of hot toluene. The filtrate was evaporated to dryness. The solid obtained was recrystallized from dichloromethane. Yield 0.64 g (25%) of orange crystalline solid.
- Anal. calc. for C30H26Cl2S2SiZr: C, 56.22; H, 4.09. Found: C, 56.41; H, 4.15.
- 1H NMR (CD2Cl2): δ 7.54-7.62 (m, 4H, 2,2′,6,6′-H of Ph), 7.49 (s, 2H, 3,3′-H of cyclopentathienyl), 7.34-7.43 (m, 4H, 3,3′,5,5′-H of Ph), 7.25-7.34 (m, 2H, 4,4′-H of Ph), 6.86 (s, 2H, 3,3′-H of cyclopentathienyl), 2.32 (s, 6H, 2,2′-Me of cyclopentathienyl), 1.09 (s, 6H, SiMe2).
- 13C{1H} NMR (CD2Cl2): δ 144.7, 137.7, 136.2, 135.7, 130.8, 130.4, 129.4, 128.6, 121.4, 120.4, 72.5, 20.7, 0.7.
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- In an argon atmosphere, to a solution of 15 mL of THF with 29.0 ml of 0.5 M ZnCl2 (14.5 mmol) in THF, 10.7 ml of 1.22 M 4-tert-butylphenylmagnesium bromide (13.0 mmol) in THF was added at ambient temperature. This mixture was stirred for 1 hour, and, then, 10.0 ml of 0.02 M Pd(PtBu3)2 (0.20 mmol, 4 mol. %) in THF and 2.43 g (5.0 mmol) of 3 were added. The resulting mixture was stirred for 5 hours at reflux. The product was isolated by flash chromatography on Silica Gel 60 (40-63 μm, d 30 mm, l 100 mm; eluent: hexanes). Yield 2.76 g (93%) of white solid of ca. 1 to 3 mixture of rac- and meso-compounds.
- Anal. calc. for C38H44S2Si: C, 76.97; H, 7.48. Found: C, 77.21; H, 7.56.
- 1H NMR (CDCl3), rac-3b: δ 7.57-7.61 (m, 4H, 3,3′,5,5′-H in C6H4), 7.42-7.46 (m, 4H, 2,2′,6,6′-H in C6H4), 7.26 (m, 2H, 5-H in cyclopenta[b]thienyl), 6.81 (m, 2H, 3,3′-H in cyclopenta[b]thienyl), 3.93 (m, 2H, 1,1′-H in cyclopenta[b]thienyl), 2.19 (d, J=1.3 Hz, 6H, 2,2′-Me in cyclopenta[b]thienyl), 1.367 (s, 18H, tBu), −0.26 (s, 6H, SiMe2); meso-3b: δ 7.55-7.59 (m, 4H, 3,3′,5,5′-H in C6H4), 7.43-7.47 (m, 4H, 2,2′,6,6′-H in C6H4), 7.23 (m, 2H, 5-H in cyclopenta[b]thienyl), 6.81 (m, 2H, 3,3′-H in cyclopenta[b]thienyl), 3.82 (m, 2H, 1,1′-H in cyclopenta[b]thienyl), 2.31 (d, J=1.3 Hz, 6H, 2,2′-Me in cyclopenta[b]thienyl), 1.363 (s, 18H, tBu), −0.23 (s, 3H, SiMe), −0.24 (s, 3H, SiMe′).
-
- In the Glove Box, to a solution of 2.49 g (4.2 mmol) of 3b in 100 ml of ether, 3.35 ml of 2.5M nBuLi (8.4 mmol) in hexanes was added at ambient temperature. This mixture was stirred for 24 hours and, then, cooled to −78° C.; 1.58 g (4.2 mmol) of ZrCl4(THF)2 was added. The resulting mixture was stirred for 24 hours at room temperature and, then, evaporated to dryness. To the residue 100 ml of toluene was added. This mixture was stirred for 8 hours at 90° C. The hot solution was filtered through a glass frit (G4). The residue was additionally washed with 3×50 ml of hot toluene. The filtrate was evaporated to dryness. The solid obtained was recrystallized from dichloromethane. Yield 0.60 g (19%) of orange crystalline solid.
- Anal. calc. for C38H42Cl2S2SiZr: C, 60.60; H, 5.62. Found: C, 60.79; H, 5.69.
- 1H NMR (CD2Cl2): δ 7.37-7.61 (m, 10H, 5,5′-H of cyclopentathienyl and 2,2′,3,3′,5,5′,6,6′-H of C6H4), 6.85 (s, 2H, 3,3′-H of cyclopentathienyl), 2.31 (s, 6H, 2,2′-Me of cyclopentathienyl), 1.29 (s, 18H, tBu), 1.09 (s, 6H, SiMe2).
- 13C{1H} NMR (CD2Cl2): δ 138.3, 138.1, 137.6, 135.6, 133.3, 130.1, 128.1, 127.4, 121.5, 120.6, 72.5, 36.1, 32.6, 20.7, 0.7.
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- In an argon atmosphere, to 29.0 ml of 0.5 M ZnCl2 (14.5 mmol) in THF, 52.0 ml of 0.25 M naphthylmagnesium bromide (13.0 mmol) in THF was added at ambient temperature. This mixture was stirred for 1 hour, and, then, 10.0 ml of 0.02 M Pd(PtBu3)2 (0.20 mmol, 4 mol. %) in THF and 2.43 g (5.0 mmol) of 3 were added. The resulting mixture was stirred for 5 hours at reflux. The product was isolated by flash chromatography on Silica Gel 60 (40-63 μm, d 30 mm, l 100 mm; eluent: hexanes). Yield 2.56 g (88%) of white solid of ca. 1 to 2 mixture of rac- and meso-compounds.
- Anal. calc. for C38H32S2Si: C, 78.57; H, 5.55. Found: C, 78.79; H, 5.66.
- 1H NMR (CDCl3), rac-3c: δ 7.25-7.96 (m, 14H, naphthyl), 7.20 (s, 2H, 5,5′-H in cyclopenta[b]thienyl), 6.26 (s, 2H, 3,3′-H in cyclopenta[b]thienyl), 3.96 (s, 2H, 1,1′-H in cyclopenta[b]thienyl), 2.06 (s, 6H, 2-Me in cyclopenta[b]thienyl), −0.22 (s, 6H, SiMe2); meso-3c: δ 7.25-7.96 (m, 14H, naphthyl), 7.17 (s, 2H, 5,5′-H in cyclopenta[b]thienyl), 6.26 (s, 2H, 3,3′-H in cyclopenta[b]thienyl), 3.84 (s, 2H, 1,1′-H in cyclopenta[b]thienyl), 2.19 (s, 6H, 2-Me in cyclopenta[b]thienyl), −0.18 (s, 3H, SiMe), −0.22 (s, 3H, SiMe′).
-
- In the Glove Box, to a solution of 2.38 g (4.1 mmol) of 3c in 100 ml of ether, 3.3 ml of 2.5M nBuLi (8.2 mmol) in hexanes was added at ambient temperature. This mixture was stirred for 24 hours and, then, cooled to −78° C.; 1.55 g (4.1 mmol) of ZrCl4(THF)2 was added. The resulting mixture was stirred for 24 hours at room temperature and, then, evaporated to dryness. To the residue 100 ml of toluene was added. This mixture was stirred for 8 hours at 90° C. The hot solution was filtered through a glass frit (G4). The residue was additionally washed with 3×50 ml of hot toluene. The filtrate was evaporated to dryness. The solid obtained was recrystallized from toluene. Yield 0.67 g (22%) of red crystalline solid.
- Anal. calc. for C38H30Cl2S2SiZr: C, 61.59; H, 4.08. Found: C, 61.68; H, 4.15.
- 1H NMR (CD2Cl2): δ 8.06 (d, J=8.4 Hz, 2H, 4,4′-H in naphthyl), 7.87 (m, 2H, 8,8′-H in naphthyl), 7.83 (d, J=8.4 Hz, 2H, 2,2′-H in naphthyl), 7.72 (dd, J=7.2 Hz, J=0.9 Hz, 2H, 5,5′-H in naphthyl), 7.53 (s, 2H, 5,5′-H in cyclopenta[b]thienyl), 7.37-7.52 (m, 6H, 3,3′,6,6′,7,7′-H in naphthyl), 6.58 (s, 2H, 3,3′-H in cyclopenta[b]thienyl), 2.34 (s, 6H, 2,2′-Me in cyclopenta[b]thienyl), 1.14 (s, 6H, SiMe2).
-
- To a mixture of 1000 ml of 96% ethanol and 94 ml of 98% H2SO4, 117 g (0.55 mol) of 2-bromo-4-isopropylaniline was added over 15 min. with vigorous stirring at −5° C. Then, a solution of 63 g of NaNO2 in 125 ml of water was added at this temperature over 1 h, and the resulting mixture was stirred for about 30 min longer. Then, 12 g of copper powder was added. The reaction mixture was refluxed for 4 h and filtered through a glass frit (G3). The filtrate was poured into 2500 cm3 of cold water. The organic product was extracted with 4×400 ml of dichloromethane. The combined extract was dried over K2CO3 and evaporated to dryness. Fractional distillation gave the title product, b.p. 64-67° C./3 mm Hg.
- Yield 117.4 g (75%) of yellowish oil.
- Anal. calc. for C9H11Br: C, 54.30; H, 5.57. Found: C, 54.44; H, 5.49.
- 1H NMR (CDCl3): δ 7.37 (m, 1H, 2-H), 7.28-7.34 (m, 1H, 5-H), 7.15-7.16 (m, 1H, 6-H), 7.14 (d, J=1.0 Hz, 1H, 2-H), 2.87 (sept, J=6.9 Hz, 1H, CHMe2), 1.24 (d, J=6.9 Hz, 6H, CHMe2).
-
- To a mixture of 34.9 g (0.26 mol) of AlCl3 and 350 ml of dichloromethane, a solution of 50.9 g (0.22 mol) of 2-bromo-2-methylpropanoyl bromide in 120 ml of dichloromethane was added dropwise with vigorous stirring at −10° C. Then, a solution of 40.0 g (0.20 mol) of 1-bromo-3-isopropylbenzene in 70 ml of dichloromethane was added dropwise at this temperature. The resulting mixture was refluxed for 12 h and then poured onto 2000 cm3 of ice. The organic product was extracted with 4×300 ml of dichloromethane. The combined extract was dried over K2CO3 and evaporated to dryness. Fractional distillation gave the title product, b.p. 130-135° C./1.5 mm Hg. Yield 36.2 g (67%).
- Anal. calc. for C13H15BrO: C, 58.44; H, 5.66. Found: C, 58.40; H, 5.67.
- 1H NMR (CDCl3): δ 7.37 (s, 1H, 6-H), 7.23 (s, 1H, 4-H), 3.31 (dd, J=16.7 Hz, J=8.0 Hz, 1H, 3-H), 2.94 (sept, J=6.8 Hz, 1H, CHMe2), 2.71 (m, 1H, 2-H), 2.65 (m, 1H, 3′-H), 1.30 (d, J=7.4 Hz, 3H, 2-Me), 1.27 (d, J=6.8 Hz, 6H, CHMe2).
-
- To a solution of 22.2 g (83.2 mmol) of 7-bromo-5-isopropyl-2-methyl-1-indanone in 120 ml of THF-methanol (2:1, vol.), 5.06 g (133 mmol) of NaBH4 was added with vigorous stirring over 3 h at 0° C. This mixture was stirred overnight at room temperature; then, 300 ml of cold water was added, and the resulting mixture was acidified with 1 M HCl to pH 1. The organic layer was separated, and the aqueous layer was extracted with 3×150 ml of dichloromethane. The combined organic fractions were dried over K2CO3 and evaporated to dryness, and 200 ml of toluene was added to the yellowish oil obtained. This toluene solution was treated with a catalytic amount of pTolSO3H (ca. 0.2 g) for 1 h at reflux, cooled to room temperature, and evaporated to dryness. The crude product was purified using flash chromatography on Silica Gel 60 (40-63 μm, d 40 mm, l 400 mm; eluent: hexanes). Yield 19.6 g (94%) of 4-bromo-6-isopropyl-2-methyl-1H-indene.
- Anal. calc. for C13H15Br: C, 62.17; H, 6.02. Found: C, 61.99; H, 6.08.
- 1H NMR (CDCl3): δ 7.20 (s, 1H, 5-H), 7.13 (s, 1H, 7-H), 6.52 (m, 1H, 3-H), 3.32 (s, 2H, 1,1′-H), 2.86 (sept, J=6.9 Hz, 1H, CHMe2), 2.12 (m, 3H, 2-Me), 1.23 (d, J=6.9 Hz, 6H, CHMe2).
- 13C{1H} NMR (CDCl3): δ 146.5, 146.4, 144.9, 143.6, 127.4, 126.5, 120.6, 113.4, 43.7, 33.9, 24.2, 16.8.
-
- In an argon atmosphere, to a solution of 10.0 g (47.8 mmol) of 4-bromo-6-isopropyl-2-methyl-1H-indene in 250 ml of diethyl ether, 29.9 ml of 1.6 M MeLi (47.8 mmol) in ether was added at 10° C. This mixture was stirred for 12 hours at 20° C. and, then, cooled to 0° C. At this temperature, 2.89 ml (3.08 g, 23.9 mmol) of Me2SiCl2 was added. The resulting mixture was stirred for 24 hours at ambient temperature; then 100 ml of water was added. The organic layer was separated, dried over K2CO3, and evaporated to dryness. The residue was treated with 25 ml of hexanes. The white solid that precipitated was filtered off, washed with 3×30 ml of hexanes, and dried in vacuum. Yield 5.47 g (41%) of white solid of ca. 1 to 1 mixture of rac- and meso-compounds.
- Anal. calc. for C38H42N2Si: C, 82.26; H, 7.63. Found: C, 82.41; H, 7.58.
- 1H NMR (CDCl3): δ 7.21-7.24 (m, 4H, 5,5′-H in indenyl of rac- and meso-compounds), 7.13 (m, 2H, 7,7′-H in indenyl of rac-compound), 7.09 (m, 2H, 7,7′-H in indenyl of meso-compound), 6.66 (m, 2H, 3,3′-H in indenyl of meso-compound), 6.63 (m, 2H, 3,3′-H in indenyl of rac-compound), 2.80-2.93 (m, 4H, CHMe2 of rac- and meso-compounds), 2.19 (m, 6H, 2,2′-Me of meso-compound), 2.17 (m, 6H, 2,2′-Me of rac-compound), 1.19-1.25 (m, 24H, CHMe2 of rac- and meso-compounds), −0.15 (s, 3H, SiMeMe′ of meso-compound), −0.21 (s, 6H, SiMe2 of rac-compound), −0.29 (s, 3H, SiMeMe′ of meso-compound).
-
- In an argon atmosphere, to a solution of 15 mL of THF with 29.0 ml of 0.5 M ZnCl2 (14.5 mmol) in THF, 13.0 ml of 1.0 M phenylmagnesium bromide (13.0 mmol) in THF was added at ambient temperature. This mixture was stirred for 1 hour, and, then, 10.0 ml of 0.02 M Pd(PtBu3)2 (0.20 mmol, 4 mol. %) in THF and 2.79 g (5.0 mmol) of 4 were added. The resulting mixture was stirred for 5 hours at reflux. The product was isolated by flash chromatography on Silica Gel 60 (40-63 μm, d 30 mm, l 100 mm; eluent: hexanes). Yield 2.71 g (98%) of white solid of ca. 1 to 1 mixture of rac- and meso-compounds.
- Anal. calc. for C40H44Si: C, 86.90; H, 8.02. Found: C, 87.11; H, 8.10.
- 1H NMR (CDCl3): δ 7.57-7.61 (m, 8H, 2,2′,6,6′-H in Ph of rac- and meso-isomers), 7.46-7.52 (m, 8H, 3,3′,5,5′-H in Ph of rac- and meso-isomers), 7.35-7.42 (m, 8H, 5,5′-H in indenyl and 4,4′-H in Ph of rac- and meso-isomers), 7.16-7.19 (m, 4H, 7,7′-H in indenyl of rac- and meso-isomers), 6.81 (m, 2H, 3,3′-H in indenyl of rac- or meso-isomer), 6.77 (m, 2H, 3,3′-H in indenyl of meso- or rac-isomer), 3.76 (s, 2H, 1,1′-H in indenyl of rac- or meso-isomer), 3.75 (s, 2H, 1,1′-H in indenyl of meso- or rac-isomer), 3.01 (sept, J=Hz, 4H, CHMe2 of rac- and meso-isomers), 2.25 (s, 6H, 2,2′-Me in indenyl of rac- or meso-isomer), 2.18 (s, 6H, 2,2′-Me in indenyl of meso- or rac-isomer), 1.30-1.35 (m, 24H, CHMe2 of rac- and meso-isomers), −0.09 (s, 3H, SiMeMe′ of meso-isomer), −0.10 (s, 6H, SiMe2 of rac-isomer), −0.16 (s, 3H, SiMeMe′ of meso-isomer).
- 13C{H} NMR (CDCl3): δ 147.0, 146.8, 145.92, 145.86, 143.95, 143.93, 141.71, 141.65, 140.9, 140.8, 133.73, 133.70, 128.9, 128.4, 126.67, 126.65, 125.73, 125.66, 124.13, 124.06, 120.45, 120.42, 47.5, 47.4, 34.21, 34.20, 24.6, 24.5, 24.4, 24.3, 18.0, 17.9, −5.13 (two resonances), −5.24.
-
- To a solution of 5.53 g (10.0 mmol) of 4a in 150 ml of ether, 8.10 ml of 2.5 M of nBuLi (20.3 mmol) in hexanes was added dropwise over 15 min at 0° C. This mixture was stirred for 12 h at room temperature and then cooled to −78° C. Next, 3.77 g (10.0 mmol) of ZrCl4(THF)2 was added. The resulting mixture was slowly (ca. 1.5 h) warmed to ambient temperature with vigorous stirring and then stirred for 24 h. The organic solvents were distilled off under reduced pressure, and 100 ml of dichloromethane was added. This mixture was filtered through a glass frit (G4). The precipitate was washed with 4×20 ml of dichloromethane and dried in vacuum. The crude product was recrystallized from toluene. This procedure gave 1.00 g (14%) of pure rac-4a@ as orange crystalline solid.
- Anal. calc. for C40H42Cl2SiZr: C, 67.38; H, 5.94. Found: C, 67.47; H, 6.00.
- 1H NMR (CD2Cl2): δ 7.60-7.65 (m, 4H, 2,2′,6,6′-H in Ph), 7.47 (m, 2H, 5,5′-H in indenyl), 7.41-7.46 (m, 3,3′,5,5′-H in Ph), 7.34-7.39 (m, 4,4′-H in Ph), 7.29 (d, J=1.2 Hz, 2H, 7,7′-H in indenyl), 6.87 (s, 2H, 3,3′-H in indenyl), 2.93 (sept, J=6.9 Hz, 2H, CHMe2), 2.26 (s, 6H, 2,2′-Me), 1.36 (s, 6H, SiMe2), 1.26 (d, J=6.9 Hz, CHMe2).
- All documents described herein are incorporated by reference herein, including any priority documents and/or testing procedures to the extent they are not inconsistent with this text. While there have been described what are presently believed to be the preferred embodiments of the present invention, those skilled in the art will realize that other and further embodiments can be made without departing from the spirit of the invention, and is intended to include all such further modifications and changes as come within the true scope of the claims set forth herein. Likewise, the term “comprising” is considered synonymous with the term “including” for purposes of Australian law.
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